Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Reexamination Certificate
2006-10-25
2008-09-09
O'Sullivan, Peter (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
C544S092000
Reexamination Certificate
active
07423146
ABSTRACT:
A process for making a compound of formula 1or a salt thereof, wherein:R1and R2are each independently H, halogen, or C1-4-alkyl, or R1and R2together are C1-6-alkylene; andR3is H, halogen, OH, C1-4-alkyl, or O—C1-4-alkyl, the process comprising:(a) reacting a compound of formula 6wherein R4is benzyl, diphenylmethyl, or trityl, each optionally substituted at, if available, an aryl group or an aliphatic carbon atom, with a compound of formula 7or a salt thereof, to obtain a compound of formula 5, or a salt thereof(b) reducing the nitro group of the compound of formula 5 to an amine group and mesylating this amine group and cleaving the protecting group during the reduction step or after the mesylation step to obtain the compound of formula 1.
REFERENCES:
patent: 4341778 (1982-07-01), Mentrup et al.
patent: 4460581 (1984-07-01), Schromm et al.
patent: 4570630 (1986-02-01), Elliott et al.
patent: 4950767 (1990-08-01), Kraatz
patent: 7220742 (2007-05-01), Lustenberger et al.
patent: 2006/0189605 (2006-08-01), Konctzki et al.
patent: 2007/0027148 (2007-02-01), Lustenberger et al.
patent: 2007/0066607 (2007-03-01), Fairhurst et al.
patent: 2007/0112191 (2007-05-01), Santagostino et al.
patent: 2008/0051392 (2008-02-01), Konetzki et al.
patent: 2008/0053430 (2008-03-01), Nowak et al.
patent: 1 165 317 (1984-04-01), None
patent: 2 164 222 (1994-12-01), None
patent: 2 232 151 (1997-04-01), None
patent: 2 233 981 (1997-04-01), None
patent: 2 237 853 (1997-06-01), None
patent: 2 300 908 (1999-04-01), None
patent: 2 450 961 (2003-01-01), None
patent: 2 425 539 (2003-04-01), None
patent: 2 425 560 (2003-04-01), None
patent: 2 471 578 (2003-08-01), None
patent: 2 472 149 (2003-08-01), None
patent: 2 474 874 (2003-08-01), None
patent: 2 552 784 (2005-08-01), None
patent: 2 562 859 (2005-11-01), None
patent: 36 09 152 (1987-09-01), None
patent: 0 043 940 (1982-01-01), None
patent: 0 237 507 (1987-09-01), None
patent: 91/14468 (1991-10-01), None
patent: 94/07607 (1994-04-01), None
patent: 94/28958 (1994-12-01), None
patent: 95/32937 (1995-12-01), None
patent: 97/12683 (1997-04-01), None
patent: 97/12687 (1997-04-01), None
patent: 97/20590 (1997-06-01), None
patent: 99/16530 (1999-04-01), None
patent: 02/30928 (2002-04-01), None
patent: 02/32898 (2002-04-01), None
patent: 03/000265 (2003-01-01), None
patent: 03/064417 (2003-08-01), None
patent: 03/064418 (2003-08-01), None
patent: 03/064419 (2003-08-01), None
patent: 2004/087142 (2004-10-01), None
patent: 2005/070908 (2005-08-01), None
patent: 2005/111005 (2005-11-01), None
patent: 2006/089859 (2006-08-01), None
E.J. Corey; Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method; Angew. Chem. Int. Ed, 1998, vol. 37 pp. 1986-2012.
Y.Hong; cis-1-Amino-2-indanol in Asymmetric Synthesis, Part 1. A Practical Catalyst System for the Enantioselective Borane Reduction of Aromatic Ketones; Tetrahedron Lett., 1994, vol. 35, NO. 36 pp. 6631-6634; Great Britain.
S. Itsuno; Asymmetric Reduction of Aliphatic Ketones with the Reagent Prepared from (S)-(-)-2-Amino-3methyl-1-1,1-diphenylbutan-1-ol and Borane; J. Org. Chem (1984) vol. 49 pp. 555-557.
G.J. Quallich; Diphenyloxazaborolidine A New Catalyst for Enantioselective Reduction of Ketones;Tetrahedron Lett (1993) vol. 34 No. 26 pp. 4145-4148; Great Britain.
S. Itsuno; Asymmetric Synthesis Using Chirally Modified Borohydrides, Part 1. Enantioselective Reduction of Aromatic Ketones with the Reagent Prepared from Borane and (S)-Valinol; J. Chem. Soc. Perkin Trans. I (1983) pp. 1673-1676.
R. Hett et al; Conformational Toolbox of Oxazaborolidine Catalysts in the Enantioselective Reduction of a-Bromo-Ketone for the Synthesis of (R,R)-Formoterol;Tetrahedron Letters (1998) vol. 39 pp. 1705-1708.
A. Hirao; Asymmetric Reduction of Aromatic Ketones with Chiral Alkoxy-amine-borane Complexes; J. Chem. Soc. Chem.Comm (1981) pp. 315-317.
G. J. Quallich; In Situ Oxazaborolidines, Practical Enantioselective Hydride Reagents;Synlett, DEc. 1993, p. 929.
M. Masui; A Practical Method for Asymmetric Borane Reduction of Prochiral Ketones Using Chiral Amino Alcohols and Trimethyl Borate; Synlett, Mar. 1997, pp. 273-274.
T. Hamada; Practical Synthesis of Optically Active Styrene Oxides via Reductive Transformation of 2-chloroacetophenones with Chiral Rhodium Catalysts; Org. Lett (2002) vol. 4 NO. 24 pp. 4373-4376.
J. Chandrasekharan; The Reduction of Oximes by Lithium Aluminum Hydride in Hexamethylphosphoramide Solvent; J. Org. Chem (1985) vol. 50 pp. 5448-5450.
J.S. Lodaya; Direct a-Mesyloxylation of Ketones and b-dicarbonyl Compounds with [Hydroxy(mesyloxy)iodo] benzene; J. Org. Chem (1988) vol. 53 p. 210.
K. Yutaka; 2-Amino-4-phenylthiazole derivatives as anti-atherogenic agents; Eur. J. Med. Chem. Chim.Ther (1981) vol. 16 pp. 355-362.
S. Kajigaeshi; z-Chloroination of Aromatic Acetyl Derivatives with Benzyltrimethylammonium Dichloroiodate; Synthesis Jul. 1988, vol. 7, pp. 545-546.
E. Vedejs; A Tyrosine-Derived Benzofuranone Related to a Diazonamide A; Org. Lett (2000) vol. 2 No. 8 pp. 1031-1032.
A. Guy; Selective a-Chloroination of Aryl Ketones; Synthesis 1982, 12, pp. 1018-1020.
A. V. Rama Rao et al; Enantioselective Catalytic reductions of Ketones with New Four Membered Oxazaborolidines: Application to (S)- Tetramisole; Tetrahedron: Asymmetry (1992) vol. 3 NO. 7 pp. 859-862; Elsevier Science Publisher.
Gerald F. Koser et al; One-Step Alpha-Tosyloxylation of Ketones with [Hydeoxy(tosyloxy)iodo]Benzene; Journal of Organic Chemistry (1982) vol. 47 No. 12 pp. 2487-2489.
Jonathan D. Bloom et al; Disodium (R,R0-5[2-[[2-(3Chlorophenyl)-2-hydroxyethyl]-amino]propyl]-1,3-benzodloxole-2,2-dicarboxylate (CL 316,243). A Potent Beta-Adrenergic Agonist Virtually Specific for Beta2 Receptors. A Promising Antidiabetic and Antiobesity Agent; Journal of medicinal Chemistry (1992) vol. 35 No. 16 pp. 3081-3084.
International Search Report and Written Opinion for corresponding international application PCT/EP2006/068157 mailed on Apr. 16, 2007.
Paula Yurkanis Bruice; Glossary: Organic Chemistry (1995) p. G-7.
International Search Report for PCT/EP2006/060033 mailed on May 4, 2006.
International Search Report for PCT/EP2007/058653 mailed Oct. 29, 2007.
International Search Report for PCT/EP2007/058654 mailed Dec. 6, 2007.
International Search Report for PCT/EP2007/058655 mailed Oct. 29, 2007.
Rall Werner
Santagostino Marco
Soyka Rainer
Boehringer Ingelheim International GmbH
Lebel Edouard G.
Morris Michael P.
O'Sullivan Peter
Witkowski Timothy X.
LandOfFree
Process for the manufacturing of pharmaceutically active... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the manufacturing of pharmaceutically active..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the manufacturing of pharmaceutically active... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3986902