Advanced route for the synthesis of cPLA2 inhibitors

Details Advanced route for the synthesis of cPLA2 inhibitors Advanced route for the synthesis of cPLA2 inhibitors

2007-08-21

2007-08-21

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C558S413000, C564S089000

Reexamination Certificate

active

11076117

ABSTRACT:
A process for making a compound of formula (I)in which process the compound HC≡C—(CH2)n—NH2is reacted with the compound R1—SO2Cl to produce an intermediate compound, which intermediate compound is then reacted with the compound of formulato produce the compound of formula (I), and compounds produced by the process of this invention. The terms R1, R2, R3, R4and n have the definitions set forth in the specification.

REFERENCES:
patent: 5053072 (1991-10-01), Ort et al.
patent: 5186736 (1993-02-01), Ort et al.
patent: 5324710 (1994-06-01), Ort et al.
patent: 5461075 (1995-10-01), O'Neill et al.
patent: 5877121 (1999-03-01), Andree et al.
patent: 6159903 (2000-12-01), Linker et al.
patent: 6339044 (2002-01-01), Andree et al.
patent: 6635771 (2003-10-01), McKew et al.
patent: 6656971 (2003-12-01), Wu et al.
patent: 6797708 (2004-09-01), McKew et al.
patent: 6812236 (2004-11-01), Gibson et al.
patent: 6812252 (2004-11-01), Ikawa et al.
patent: 6891065 (2005-05-01), Wu et al.
patent: 6984735 (2006-01-01), McKew et al.
patent: 2002/0127605 (2002-09-01), Hamilton et al.
patent: 2003/0144282 (2003-07-01), McKew et al.
patent: 2003/0149029 (2003-08-01), McKew et al.
patent: 2003/0158405 (2003-08-01), McKew et al.
patent: 2003/0166649 (2003-09-01), McKew et al.
patent: 2004/0082785 (2004-04-01), McKew et al.
patent: 2004/0242456 (2004-12-01), Luthy et al.
patent: 2005/0020858 (2005-01-01), Wu et al.
patent: 2005/0049296 (2005-03-01), Dehnhardt et al.
patent: 2005/0070723 (2005-03-01), Dehnhardt et al.
patent: 2005/0148770 (2005-07-01), Michalak et al.
patent: 2005/0159613 (2005-07-01), Wu et al.
patent: 2006/0014759 (2006-01-01), McKew et al.
patent: 0401903 (1990-05-01), None
patent: 02115157 (1990-04-01), None
patent: WO91/06541 (1991-05-01), None
patent: WO93/15047 (1993-08-01), None
patent: WO95/17391 (1995-06-01), None
patent: WO96/07647 (1996-03-01), None
patent: WO97/05117 (1997-02-01), None
patent: WO97/26248 (1997-07-01), None
patent: WO97/30980 (1997-08-01), None
patent: WO 02/20487 (2002-03-01), None
patent: WO 02/44126 (2002-06-01), None
patent: WO 02/059080 (2002-08-01), None
patent: WO 03/022051 (2003-03-01), None
patent: WO 03/048122 (2003-06-01), None
patent: WO 2005/012238 (2005-02-01), None
Agnola et al., Solid-Phase Synthesis of Indoles Using the Palladium-Catalysed Coupling of Alkynes with Iodoaniline Derivatives, Tetrahedron Letters,(1997), vol. 38, No. 13, pp. 2307-2310.
Appleton et al., A Mild and Selective C-3 Reductive Alkylation of Indoles, Tetrahedron Letters, (1993), vol. 34, No. 9, pp. 1529-1532.
Deng et al., Synthesis and Characterization of Poly(N-propargylsulfamides), Macromolecules,(2004), vol. 37, No. 15, pp. 5538-5543.
Nilsson, B. et al, Derivates of the Muscarinic Agent N-Methyl-N-(methyl-4-pyrrolidino-2-butynyl)acetamide, J. Med. Chem. (1988), vol. 31, pp. 577-582.
Fujiwara, J. et al, Nucleophilic Aromatic Substitution by Organoaluminum Reagents, J. Am. Chem. Soc., (1983) vol. 105, pp. 7177-7179.
International Search Report for International application No. PCT/US2004/023247.
Database Caplus Chemical Abstracts Service, Columbus, Ohio, US; database accession No. 1990-532816.
Chung J. et al., “A Practical Synthesis of Fibrinogen Receptor Antagonist MK-383. Selective Functionalization of (S)-Tyrosine”, Tetrahedron Letters (1993), vol. 49, No. 26, pp. 5767-5776, Pergamon Press Ltd., printed in Great Britain.
Ezquerra J. et al., “Efficient reagents for the Synthesis of 5-, 7-, and 5, 7-Substituted Indoles Starting from Aromatic Amines: Scope and Limitations”, J. Org. Chem., vol. 61, 1996, 5804-5812.
Gandolfi C. et al., “N-Acyl-2-substituted-1,3-thiazolidines, a New Class of Non-narcotic Antitussive Agents; Studies Leading to the Discovery of Ethyl 2-[(2-Methoxyphenoxy)methyl]-β-oxothiazolidine-3-propanoate”, J. Med. Chem. (1995), 38, pp. 508-525.
Hoffmann K. et al., “Fibrin-Stabilizing Factor Inhibitors. 12. 5-Dibenzylaminopentylamine and Related Compounds, a New Type of FSF Inhibitors”, Journal of Medicinal Chemistry (1975), vol. 18, No. 3, pp. 278-284.
Iyer S. et al., “Regiospecific Synthesis of 2-Methoxy-3-methyl-1,4-benzoquinones from Maleoylcobalt Complexes and Alkynes via Lewis Acid Catalysis. A Highly Convergent Route to Isoquinoline Quinones”, J. Am. Chem. Soc. (1987), 109, pp. 2759-2770.
Orazi O. et al., “Synthesis of Fused Heterocycles: 1,2,3,4-Tetrahydroisoquinolines and Ring Homologues via Sulphonamidomethylation”, J. Chem. Soc. Perkin Trans. I (1986), pp. 1977-1986.
Pierce et al., “Practical Asymmetric Synthesis of Efravirenz (DMP 266), and HIV-1 Reverse Transcriptase Inhibitor”, J. Org. Chem. (1998), vol. 63, pp. 8536-8543.
Sakamoto T et al., “Condensed Heteroaromtic Ring Systems, XIII. One-Step Synthesis of 2-Substituted 1-Methylsulfonylindoles from N-(2-Halopenyl)methanesulfonamides” Chem. Pharm. Bull. (1998), 36(4) pp. 1305-1308.
Shin K. et al., “An Expeditious Synthesis of 2,2′-Biindolyl”, Synlett (1995) Aug. pp. 859-860.
Taylor E. et al., Novel 5-Desmethylene Analogues of 5, 10-Dideaza-5,6,7,8-tetrahydrofolic Acid as Potential Anticancer Agents:, J. Org. Chem. (1992), 57, pp. 3218-3225.
Villemin et al., “Palladium Homogenous and Supported Catalysts: Synthesis and Functional Acetylenics and Cyclisation to Heterocycles” Heterocycles (1989), vol. 29, No. 7, pp. 1255-1261.
Watson, S.E., et al., “Novel Methodology for the Preparation of 5-Substituted Tetrahydro[2,3-D]Pyrimidines”, Synthetic Communications (1998), 28(1), pp. 1897-1905.
Xiao et al., Regioselective Carbonylative Heteroannulation of o-lodothiophenols with Allenes and Carbon Monoxide Catalyzed by a Palladium Complex: A Novel and Efficient Access to Thiochroman-4-one Derivatives, J. Org. Chem. (1999), vol. 64, pp. 9646-9652.
Ziegler et al., “The Preparation of Alkanesulfonyl Halides”, From the Department of Organic Chemistry, Research Division, Sharp and Dohme, Inc., 1951, vol. 16, pp. 621-625.
Written Opinion of the International Searching Authority for International Application No. PCT/US2005/029338, 6 pages, 2005.
International Search Report for International Application No. PCT/US2005/029338, 4 pages, 2005.

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