Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2006-06-13
2006-06-13
Saeed, Kamal A. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C564S510000, C568S683000
Reexamination Certificate
active
07060850
ABSTRACT:
The present invention includes methods and compositions for increasing the fluorous nature of an organic compound by reacting it with at least one fluorous compound to produce a fluorous tagged organic compound. The increased fluorous nature of the fluorous tagged organic compound can then be utilized to separate the fluorous organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom. The resultant fluorous tagged organic compound can be subjected to subsequent chemical transformations, wherein the fluorous nature of the tagged compound is utilized to increase the ease of separation of the fluorous tagged organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom, after each chemical transformation. The chemical transformations result in a second fluorous tagged organic compound wherein the fluorous nature of the second fluorous tagged organic compound can then be reduced by removing the fluorous group therefrom, thereby producing a second organic compound that may be employed as a pharmaceutical compound or intermediate, or a combinatorial library component.
REFERENCES:
patent: 4022897 (1977-05-01), Yale et al.
patent: 4098894 (1978-07-01), Buchel et al.
patent: 4745191 (1988-05-01), Husbands
patent: 5236923 (1993-08-01), Kirsten et al.
patent: 5463082 (1995-10-01), Horvath et al.
patent: 5777121 (1998-07-01), Curran et al.
patent: 5859247 (1999-01-01), Curran et al.
patent: 6156896 (2000-12-01), Curran et al.
patent: 6600074 (2003-07-01), Onishi et al.
patent: 6749756 (2004-06-01), Curran et al.
patent: 2002/0183521 (2002-12-01), Curran et al.
patent: 2003/0078444 (2003-04-01), Curran et al.
patent: 2003/0125590 (2003-07-01), Curran et al.
patent: 1925555 (1971-01-01), None
patent: 0 248 697 (1987-12-01), None
patent: 0328111 (1989-08-01), None
patent: 0 354 297 (1990-02-01), None
patent: 0 468 531 (1992-01-01), None
patent: 0628316 (1994-12-01), None
patent: 1143481 (1969-02-01), None
patent: 1269096 (1972-03-01), None
patent: 58-057325 (1983-04-01), None
patent: 62205350 (1987-09-01), None
patent: 62278551 (1987-12-01), None
patent: 63-239254 (1988-10-01), None
patent: 07207021 (1995-08-01), None
patent: WO 97/01562 (1997-01-01), None
patent: WO 98/25916 (1998-06-01), None
patent: WO 00/18774 (2000-04-01), None
patent: WO 01/61332 (2001-08-01), None
Schwinn et al., 2002, Helvetica Chimica Acta, 85(1): 255-264.
Schwinn et al., 2002, CAS: 137:32933.
International Search Report from PCT/US03/21686, International Filing Date Nov. 7, 2003, Fluorous Technologies.
Kiss, et al., “An improved design of fluorophilic molecules: prediction of the In P fluorous partition coefficient, fluorophilicity, using 3D QSAR descriptors and neural networks”; Journal of Fluorine Chemistry, 108 (2001) 95-109.
Kleijn, et al., “Synthesis of Arylzinc Thiolates Containing Perfluoroalkyl Chains. Model Catalyst Precursors for the Enantioselective Zinc-Mediated 1,2-Addition of Dialkylzincs to Aldehydes in Fluorous Biphase Systems”; Organic Letters, (1999), vol. 1(6), 853-855.
Schwinn, et al., “Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems”; Helvetica Chimica Acta, vol. 85 (2002), 255-264.
Filippov, et al., “Use of benzyloxycarbonyl (Z)-based fluorophillic tagging reagents in the purification of synthetic peptides”; Tetrahedron Letters, 43 (2002) 7809-7812.
Curran, et al., “Synthesis and Reactions of Fluorous Carbobenzyloxy (FCbz) Derivatives of α-Amino Acids”; Journal of Organic Chemistry, (2003), 68, 4643-4647.
Brown, et al., “Preparation of N-1, 1-dl-H-perfluoroalkyl Amines”; Journal of Organic Chemistry, (1957), 22, 454.
Allouch, et al., “Synthèses et réactivité avec des nucléophiles de sels de perfluoroalkylméthylèneoxy(trisdiméthylamino) phosphonium”; Journal of Fluorine Chemistry, 66 (1994) 31-38.
Billard, et al., “Reactivity of Stable Trifuoroacetaldehyde Hemiaminals. 2. Generation and Synthetic Potentialities of Fluorinated Iminiums”; J. Org. Chem., (2002), 67, 997-1000.
Lindsley, et al., “Fluorous-tethered quenching reagents for solution phase parallel synthesis”; Tetrahedron Letters, 43 (2002) 4225-4228.
Trabelsi, et al., “Synthèse de glycosides et de nucléosides F-alkylés”; Journal of Fluorine Chemistry, 56 (1992) 105-107.
Jouani, et al., “Synthèse des isocyanates de 2-F-alkyléthyle”; Journal of Fluorine Chemistry, 56 (1992) 85-92.
Lindsley, et al., “Fluorous-tethered amine bases for organic and parallel synthesis: scope and limitations”, Tetrahedron Letters, 43 (2002) 6319-6323.
Zhang, et al., “Fluorous elecctrophilic scavengers for solution-phase parallel synthesis”, Tetrahedron Letters, 44 (2003) 2065-2068.
U.S. Appl. No. 09/506,779, Curran et al.
U.S. Appl. No. 09/565,087, Curran et al.
U.S. Appl. No. 09/583,247, Wipf et al.
U.S. Appl. No. 09/602,105, Curran et al.
U.S. Appl. No. 09/932,903, Curran et al.
Curran, Strategy-Level Separations in Organic Synthesis: From Planning to Practice, Angew. Chem., Int. Ed. Eng., 1998, 37, 1175-1196.
Flynn, Phase-Trafficking Reagents and Phase-Switching Strategies for Parallel Synthesis, Med. Res. Rev., 1999, 19, 408-431, John Wiley & Sons, Inc.
Kaldor et al., Combinatorial chemistry using polymer-supported reagents, Curr. Opin. Chem. Bio., 1997, 1, 101-106.
Shuttleworth et al., Functionalised Polymers: Recent Developments and New Applications in Synthetic Organic Chemistry, Synthesis, 1997, 1217-1239.
Ley et al., Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation, J. Chem. Soc., Perkin Trans. 1, 2000, 3815-4195.
Eames et al., Polymeric Scavenger Reagents in Organic Synthesis, Eur. J. Org. Chem., 2001, 1213-1224.
Danielson et al., Fluoropolymers and fluorocarbon bonded phases as column packings for liquid chromatography, J. Chromat., 1991, 544, 187-199, Elsevier Science Publishers B.V.
Curran, Fluorous Reverse Phase Silica Gel. A New Tool for Preparative Separations in Synthetic Organic and Organofluorine Chemistry, Synlett, 2001, 9, 1488-1496.
Zhang, Fluorous Synthesis of Disubstituted Pyrimidines, Org. Lett., 2003, 5, 1011-1013.
Chen et al., FluoMar, a Fluorous Version of the Marshall Resin for Solution-Phase Library Synthesis, Org. Lett., 2003, 5, 1015-1017.
Zhang et al., Fluorous electrophilic scavengers for solution-phase parallel synthesis, Tet. Lett., 2003, 44, 2065-2068.
Orain et al., Protecting Groups in Solid-Phase Organic Synthesis, J. Combinatorial Chem., 2002, 4, 1-16.
Studer et al., Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis, Science, 1997, 275, 823-826.
Studer et al., A Strategic Alternative to Solid Phase Synthesis: Preparation of a Small Isoxazoline Library by “Fluorous Synthesis”, Tetrahedron, 1997, 53, 6681-6696.
Studer et al., Fluorous Synthesis: Fluorous Protocols for the Ugi and Biginelli Multicomponent Condensations, J. Org. Chem., 1997, 62,-2917-2924.
Curran et al., Preparation of a Fluorous Benzyl Protecting Group and Its Use in a Fluorous Synthesis Approach to a Disaccharide, Tet. Lett., 1998, 39, 4937-4940.
Curran et al., Fluorous Synthesis with Fewer Fluorines (Light Fluorous Synthesis): Separation of Tagged from Untagged Products by Solid-Phase Extraction with Fluorous Reverse-Phase Silica Gel, J. Am. Chem. Soc., 1999, 121, 9069-9072.
Zhang et al., Separation of “Light Fluorous” Reagents and Catalysts by Fluorous Solid-Phase Extraction: Synthesis and Study of a Family of Triarylphosphines Bearing Linear and Branched Fluorous Tags, J. Org. Chem., 2000, 65, 8866-8873.
Luo et al., Fluorous Boc (FBoc) Carbamates: New Amine Protecting Groups for Use in Fluorous Synthesis, J. Org. Chem., 2001, 66, 4261-4266.
Luo et al., Fluorous Mixture Synthesis: A Fluorous-Tagging Strategy for the Synthesis and Sep
Chen Christine Hiu-Tung
Luo Zhiyong
Nagashima Tadamichi
Yu Marvin S.
Zhang Wei
Fluorous Technologies Incorporated
Kirkpatrick & Lockhart Nicholson & Graham LLP
Saeed Kamal A.
Shiao Robert
LandOfFree
Fluorous tagging and scavenging reactants and methods of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fluorous tagging and scavenging reactants and methods of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fluorous tagging and scavenging reactants and methods of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3709898