Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur halides
Reexamination Certificate
2006-07-20
2010-11-30
Anderson, Rebecca L (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur halides
C562S828000
Reexamination Certificate
active
07842834
ABSTRACT:
The present invention provides synthetic processes for the preparation of sulfonyl halides of Formula Ar—(R)z—SO2—X and sulfonamides of Formula Ar—(R)z—SO2—NR4R5, where the constituent variables are as defined herein, that are useful as intermediates in the preparation of pharmaceuticals.
REFERENCES:
patent: 2199568 (1940-05-01), Lange et al.
patent: 2507408 (1950-05-01), Jacob
patent: 2888486 (1959-05-01), Gregory
patent: 4885027 (1989-12-01), Pomidor
patent: 7321061 (2008-01-01), Michalak et al.
patent: 2005/0187408 (2005-08-01), Michalak et al.
patent: 48 722 (1889-08-01), None
patent: 150 313 (1904-03-01), None
patent: WO03/048122 (2003-06-01), None
patent: WO 2005070904 (2005-08-01), None
patent: WO2005/082843 (2005-09-01), None
patent: WO2007/013974 (2007-02-01), None
Abdellaoui et al., “Synthesis of the naphthalenic bioisostere of the anti-migraine drug sumatriptan,”Synthetic Communications(1995) 25(9):1303-1311.
Abramovitch et al., “Solution and Flash Vacuum Pyrolysis of Some 2,6-Disubstituted β-Phenethylsulfonyl Azides and of β-Styrenesulfonyl Azide,”J. Org. Chem., 50:2066-2073 (1985).
Beilstein Registry No. 1747453, “ethanesulfonic acid methylamide, N-methyl-ethanesulfonamide,” 1 page, 2008.
Beilstein Registry No. 2639938, “N-ethyl-cyclohexanesulfonamide,” 1 page, 2008.
Beilstein Registry No. 2697078, “2-trifluoromethylbenzenesulfonamide,” 3 pages, 2008.
Beilstein Registry No. 2702138, “4-Amino-2-trifluormethyl-benzolsulfonsaeure-(N-isopropyl-amid),” 2 pages, 2008.
Beilstein Registry No. 2703228, “4-Amino-2-trifluormethyl-benzolsulfonsaeure-(N-butyl-amid),” 2 pages, 2008.
Beilstein Registry No. 2717732, “2-Cyclohexyl-aethan-sulfonamid,” 1 page, 2008.
Beilstein Registry No. 3255360, “3-phenyl-propane-1-sulfonic acid amide,” 1 page, 2008.
Beilstein Registry No. 5427164, “N-methyl 2-phenylethanesulfonamide,” 1 page, 2008.
Brundish et al., “Design and Synthesis of Thrombin Inhibitors: Analogues of MD-805 with Reduced Stereogenicity and Improved Potency,”J. Med. Chem., 42:4584-4603 (1999).
Dmowski et al., “A Site Selective Functionalisation of 1,3-Bis(trifluromethyl)benzene,”Tetrahedron, (1998) 54:6781-92.
L. Field, “Aromatic Sulfonic Acid Anhydrides,”Journal of the American Society(Jan. 1952) 74:394-98.
Freeman et al., “Intermediates in a peroxy acid oxidation of phenyl phenylmethanethiosulfinate1,2,”J Organic Chemistry(1981) 46(20):3991-3996.
Hartman et al., “Synthesis and derivatization of novel 4-aroylthiophene-and furan-2-sulfonamides,”J Heterocyclic Chemistry(1989) 26(6):1793-1798.
“Herstellung aromatischer Sulfonsäurechloride,”Houben-Weyl: Methoden der Organischen Chemie, 4th Edition, George Thieme Verlag, Stuttgart, Germany, p. 563 (1955).
Huang et al., “Facile Synthesis of Sulfonyl Chlorides,”Tetrahedron Letters, (1992) 33(19): 2657-60.
Kirk-Othmer,Kirk-Othmer Encyclopedia of Chemical Technology, 5thedition; www3.interscience.wiley.com/cgi-bin/mrwhome/104554789/home, 2006.
Khorana, H. G., “Carbodiimides: Part II. The Reaction of Sulphonic Acids with Carboniimides. A New Method of Preparation of Sulphonic Anhydrides,”Canadian Journal of Chemistry(1953) 31:585-88.
Leung et al., “The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors,”Bioorganic&Medicinal Chemistry(2002) 10(7): 2309-2323.
Lichtenberger et al., “Sur les di-esters sulfoniques,”Bulletin de la Societe Chimique de France, (1961) 363-371.
J. March, “Advanced Organic Chemistry,” John Wiley & Sons, New Jersey; 4th edition (Dec. 1992); p. 499.
Nakayama et al., “Reaction of Arylmethanesulfonyl and Styrylmethanesulfonyl Chlorides with Triethylamine,”Tetrahedron Letters, (1984) 25(40):4553-56.
Rewcastle et al., “Potential antitumor agents. 63. Structure-activity relationships for side-chain analogues of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid,”J Medicinal Chemistry(1991) 34(9):2864-2870.
Remington's Pharmaceutical Science, 17thedition, Easton, PA, 1985; p. 1418.
International Search Report dated Jun. 8, 2005 for International Application No. PCT/US2005/005624.
International Search Report for PCT/US2006/028182, 6 pages (Jan. 24, 2007).
Written Opinion of the International Searching Authority for PCT/US2006/028182, 8 pages (Jan. 24, 2007).
Helom Jean L.
Michalak Ronald S.
Zeldis Joseph
Anderson Rebecca L
Kispert Jennifer A.
Nolan Jason M
Ronau Robert T.
Wyeth LLC
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