Selective N-sulfonylation of 2-amino fluoro- and...

Details Selective N-sulfonylation of 2-amino fluoro- and... Selective N-sulfonylation of 2-amino fluoro- and...

2007-02-15

2010-11-23

Loewe, Sun Jae Y (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C549S064000

Reexamination Certificate

active

07838550

ABSTRACT:
Processes for preparing sulfonamide trifluoroalkyl substituted alcohol compounds are provided. Desirably, the compounds are heterocyclic sulfonamide trifluoroalkyl substituted alcohol compounds or phenyl sulfonamide trifluoroalkyl substituted alcohol compounds.

REFERENCES:
patent: 5795890 (1998-08-01), Nakae et al.
patent: 5962231 (1999-10-01), Yue et al.
patent: 6362178 (2002-03-01), Niewohner et al.
patent: 6476029 (2002-11-01), Niewohner et al.
patent: 6610734 (2003-08-01), Kreft et al.
patent: 6657070 (2003-12-01), Resnick
patent: 6667342 (2003-12-01), Clarke et al.
patent: 6683081 (2004-01-01), Niewohner et al.
patent: 6800764 (2004-10-01), Kreft et al.
patent: 6803365 (2004-10-01), Niewohner et al.
patent: 6878742 (2005-04-01), Kreft et al.
patent: 7166622 (2007-01-01), Kreft et al.
patent: 7687666 (2010-03-01), Chan et al.
patent: 2003/0013892 (2003-01-01), Resnick
patent: 2004/0006050 (2004-01-01), Kreft et al.
patent: 2004/0063737 (2004-04-01), Lucking et al.
patent: 2004/0198778 (2004-10-01), Kreft et al.
patent: 2005/0171180 (2005-08-01), Resnick et al.
patent: 2007/0037778 (2007-02-01), Kreft et al.
patent: 769498 (1997-04-01), None
patent: 09241262 (1997-09-01), None
patent: 11343279 (1999-12-01), None
patent: WO-03-063797 (2003-08-01), None
patent: WO-03/076437 (2003-09-01), None
patent: WO-03/088908 (2003-10-01), None
patent: WO-03/103660 (2003-12-01), None
patent: WO-2004/078731 (2004-09-01), None
patent: WO-2004/092155 (2004-10-01), None
Berry et al., “A Convenient Method for the Preparation of Enantiomerically Pure 2-Substituted N-Tosylaziridines”, Synlett., 1:41-44 (Jan. 1992).
Bowman et al., “A Facile Method for the N-Alkylation of α-Amino Esters”, Tet. 53(46):15787-15798 (Nov. 17, 1997).
Chataigner et al., “Discovery of a New Efficient Chiral Ligand for Copper-Catalyzed Enantioselective Michael Additions by High-Throughput Screening of a Parallel Library”, Ang. Chem. Int. Ed., 39(5):916-918 (Mar. 3, 2000).
Cintrat et al., “Preparation of Chiral 2-Stannyloxazolidines and First Considerations on the Transacetalisation Reaction Mechanism”, Eur. J. Org. Chem, 20:4251-4267 (Oct. 2004).
Egboh et al., “Synthesis and Characterization of Some Polyurethane Ionomers”, Polymer, 23(8):1167-1171 (Jul. 1982).
Gandon et al., “Tris(trimethylsilyl)silane: An Unprecedented Enhancement in the Diastereoselectivity of Radical Cyclisations to Give 2,4-Disbstituted Piperidines”, Org. & Biomolec. Chem. 2(16):2270-2271 (2004; Epub date Jul. 19, 2004).
Ghosh et al., “Chelation-controlled Ester-Derived Titanium Enolate Aldol reaction: Diastereoselective syn-aldols with mono- and Bidentate Aldehydes”, Tet. Lett., 43(32):5621-5624 (Aug. 5, 2002).
Fuji et al., “Ring Opening of Optically Active CIS-Disubstituted Aziridino Alcohols: An Enantiodivergent Synthesis of Functionalized Amino Alcohol Derivatives”, Heterocycles, 42(2):701-722 (1996).
Hedley et al., “Development of a [3+3] Cycloaddition Strategy Toward Functionalized Piperidines”, J. Org. Chem., 68(11):4286-4292 (Jan. 3, 2003: Epub date Apr. 22, 2003).
Hudlicky et al., “JOC Additions and Corrections”, J. Org. Chem, 68(2):674 (2003: Epub date Jan. 1, 2003).
Hudlicky et al., “Total Synthesis and Biological Evaluation of Amaryllidaceae Alkaloids: Narciclasine, ent-7-Deoxypancratistatin, Regioisomer of 7-Deoxypancratistatin, 10b-epi-Deoxypancratistatin, and Truncated Derivatives”, J. Org. Chem., 67(25):8726-8743 (2002: Epub date Jul. 26, 2002).
Ibuka et al., “Aza-Payne Rearrangement of Activated 2-Aziridinemethanols and 2,3-Epoxy Amines Under Basic Conditions”, J. Org. Chem., 60(7):2044-2058 (1995).
Ibuka et al., “Unprecedented Rearrangement Reaction of 2-Aziridinemethanols with “Lower Order” Lithium Methylcyanocuprate”, Tet. Lett., 34(46):7421-7424 (Nov. 12, 1993).
Ibuka et al., “A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alky1-2-Vinylaziridines over Their 2,3-Trans-Isomers: Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres”, J. Org. Chem., 62(4):999-1015 (1997).
Moran et al., “A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine”, Org. Lett., 5(19):3427-3429 (Jun. 23, 2003: Epub date Aug. 28, 2003).
Ohno et al., “A 2,3-Cis-Selective Synthesis of Aziridines Bearing a Vinyl Group from Allyl Methyl Carbonates and Allyl Mesylates”, J. Chem. Soc, Perkin Trans. 1, 22:3703-3716 (1998).
Ohno et al., “Stereodivergent Synthesis of Chiral 2-Alkenylaziridines: Palladium(0)-Catalyzed 2,3-cis-Selctive Aziridination and Base-Mediated 2,3-trans-Selective Aziridination”, Chem. & Pharm. Bull., 52(1):111-119 (Jan. 2004).
Ohno et al., “Palladium(0)-Catalyzed Stereoselective Cyclization of Allenenes: Divergent Synthesis of Pyrrolidines and 3-Azabicyclo[3.1.0]Hexanes from Single Allenenes”, J. Org. Chem., 69(13):4541-4544 (2004: Epub date May 28, 2004).
Otsuka et al., “Catalytic Asymmetric Reduction of Acetophenone Using Optically Active N-Sulfonyloxazaborolidine as a Catalyst”, Memoirs of the Faculty of Science, Kyushu Univ., Series C: Chemistry 19(1):23-28 (1993).
Su et al., “Stereochemical Diversity Through Cyclodimerization: Synthesis of Polyketide-like Macrodiolides”, Org. Lett., 5(12):2149-2152 (2003: Epub date May 15, 2003).
Tanner et al., “Studies of Regio- and Stereoselectivity in Some Nucleophilic Ring Opening Reactions of N-Tosyl-3-Phenyl-2- Aziridinemethanols and Derivatives”, Tet. 51(30):8279-8288 (Jul. 24, 1995).
Tanner et al., “Regioselective Nucleophilic Ring Opening of 2,3-Aziridino Alcohols”, Tet. 48(29):6069-6078 (1992).
Takahashi et al., “Synthesis and Absolute Configuration of Optically Pure 4-Isopropyl-N-Tosyl-1,3-Oxazolidines”, Heterocycles 33(1):281-290 (1992).
Wanner et al., “A Dual Metathesis Route to Oligomeric Sulfonamides”, Tet. Lett., 43(6):917-921 (Feb. 4, 2002).
Atsushi, “3-Oxa-2,7-diazabicyclo(3.3.0)octane Derivative”, English abstract of Japanese Patent No. 09-241262 (Sep. 16, 1997).
Shionogi & CO LTD., “Sulfonamide Derivatives are TNF-α Inhibitors”, English abstract of Japanese Patent No. 11-343279 (Dec. 14, 1999).
Chemical Diversity Research Institute, “Quinoline-Carboxylic Acids and the Derivatives Thereof, A Focused Library”, English abstract of International Patent Publication No. WO-2004/078731.
Tanner et al., “Enanoselective Routes toward 1β-Methylcarbapenems from Chiral Aziridines”, Tetrahedron, 48(29):6079-6086, (1992).
Otsuka et al., “Borane O-Adduct can be an intermediate in Chiral N-Sulfonyloxazaborolidine-Catalyzed Enantioselective Reduction of Ketones”, SYNLETT, (May 1995).
Abiko et al., “New isoxazolidine-based chiral auxiliaries for asymmetric syntheses”, Tetrahedron Letters, 38(18):3261-3264 (1997).
Reddy et al., “A practical protocol for chemoselective N-methylation of vicinal amino alcohols”, Tetrahedron Letters, 41:949-951 (2000).
Altava et al., “A general route for the preparation of polymer-supported N-tosyl aminoalcohols and their use as chiral auxiliaries”, Tetrahedron Letters, 42:1673-1675 (2001).
Brüggeman et al., “Stereoselective formation of quaternary carbon centres with chiral 3-sulfonyl-1,3-oxazolidines and titanium enolates”, Tetrahedron, 58:321-340 (2002).
Bartels et al., “Asymmetric lr1-Catalysed Allylic Alkylation of monosubstituted allylic acetates with phosphorus amidites as ligands”, Eur. J. Org. Chem., 1097-1103 (2003).
Ohno et al., “Synthesis of Allenes from Allylic alcohol derivatives bearing a bromine atom using a palladium(0)/Diethylzinc system”, J. Org. Chem., 67(4):1359-1367 (Feb. 22, 2002).
Aversa et al., 

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