Nitrogen-containing heterocycles

Details Nitrogen-containing heterocycles Nitrogen-containing heterocycles

2005-08-09

2005-08-09

Wilson, James O. (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S219000, C546S220000

Reexamination Certificate

active

06927294

ABSTRACT:
Functionalized nitrogen heterocyclic compounds, including benzodiazepines and azasugars, and synthetic methods for preparing such compounds. Nitrogen-containing heterocycles are prepared by reacting amino-carbonyl compounds that contain an amine moiety connected via a linker to a carbonyl moiety with an organoboron derivative.

REFERENCES:
patent: 4442099 (1984-04-01), Nicolaou et al.
patent: 4567290 (1986-01-01), Nicolaou et al.
patent: 4710521 (1987-12-01), Soukup et al.
patent: 4759880 (1988-07-01), Nicolaou et al.
patent: 5087790 (1992-02-01), Petasis et al.
patent: 5136501 (1992-08-01), Silverman et al.
patent: 5177046 (1993-01-01), Savoca et al.
patent: 5276120 (1994-01-01), Wong et al.
patent: 5594732 (1997-01-01), Bell et al.
patent: 5752238 (1998-05-01), Dedrick
patent: 5756789 (1998-05-01), Bruce et al.
patent: 5842040 (1998-11-01), Hughes et al.
patent: 5845265 (1998-12-01), Woolston
patent: 5870717 (1999-02-01), Wiecha
patent: 5878400 (1999-03-01), Carter, III
patent: 5878423 (1999-03-01), Anderson et al.
patent: 5890138 (1999-03-01), Godin et al.
patent: 5896379 (1999-04-01), Haber
patent: 5946467 (1999-08-01), Pathakis et al.
patent: 6030715 (2000-02-01), Thompson et al.
patent: 6030917 (2000-02-01), Weinberg et al.
patent: 6069109 (2000-05-01), Kao et al.
patent: 6232467 (2001-05-01), Petasis et al.
patent: 6259699 (2001-07-01), Opalka et al.
patent: 6272474 (2001-08-01), Garcia
patent: 6336105 (2002-01-01), Conklin et al.
patent: 6336138 (2002-01-01), Caswell et al.
patent: 6377937 (2002-04-01), Paskowitz
patent: 6397212 (2002-05-01), Biffar
patent: 6415270 (2002-07-01), Rackson et al.
patent: 6427132 (2002-07-01), Bowman-Amuah
patent: 6602817 (2003-08-01), Petasis
patent: 2003/0236423 (2003-12-01), Petasis
patent: 0 736 509 (1996-10-01), None
patent: 0 736 509 (2001-11-01), None
patent: WO 97/19415 (1997-05-01), None
patent: WO 98/19259 (1998-05-01), None
patent: WO 98/35469 (1998-08-01), None
patent: WO 99/06913 (1999-02-01), None
patent: WO 99/13417 (1999-03-01), None
Nugent, William A., “Chiral Lewis Acid Catalysts. Enantioselective Addition of Azide to Meso Epoxides” J. Am. Chem. Soc., vol 114(7), pp. 2668-2769 (1992).
Butters et al, “Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis” Tetrahedron: Asymmetry, vol. 11, pp. 113-124 (2000).
Mao et al, “Synthesis of 1-deoxymannojirimycin analogues using N-tosyl and N-nosyl activated aziridines derived from 1-amino deoxyglucitol” Tetrahedron, vol. 57, pp. 6955-6967 (2001).
van den Broek et al, “Synthesis of oxygen-substituted N-alkyl 1-deoxynorjirimycin derivatives: aza sugar alpha-glucosidase inhibitors showing antiviral (HIV-1) and immunosuppressive activity” Recl. Trav. Chim. Pays-Bas, vol. 113(110) pp. 507-516 (1994).
Shilvock et al, “Ihibition of Naringinase (L-Rhamnosidase) by Piperidine Analogues of L-Rhamnose: Scaffolds for Libraries Incorporating Trihydroxypipecolic acids” Tetrahedron Letters, vol. 37(47) pp. 8569-8572 (1996).
Lee et al, Inhibition of UDP-Gal Mutase and Mycobacterial Galactan Biosynthesis by Pyrrolidine Analogues of Galactofuranos Tetrahedron Letters, vol. 38(38) pp. 6733-6736 (1997)
Luna et al, “Stereoselective Ring Opening of meso Bicyclic Hydrazines: A Straightforward Approach to Hydrazino Cyclopenten Cores” Organic Letters, vol. 5(25), pp. 4771-4774 (2003).
Babine, R. E. and S.L. Bender., “Molecular Recognition of Protein-Ligand Complexes: Applications to Drug Design,”Chem. Rev. 97:1359-1472 (1997).
Bhaley, G. et al., “Solid-Phase Synthesis of Diverse Tetrahydro-1,4-Benzodiazepine-2-ones,”Tetrahedron Letters38(48):8375-8378 (1997).
Bläser, E. et al., “Asymmetric Steering of Oxa Diels—Alder Reactions with Silyloxydienes Employing Proline Esters as Chiral Auxiliary Groups,”Eur. J. Org. Chem., 329-333, (1999).
Deloux, Laurent and Morris Srebnik “Asymmetric Boron-Catalyzed Reactions”,Chem. Rev. 93:763-784, (1993).
Durantel. et al., “Study of the Mechanism of Antiviral Action of Iminosugar Derivatives against Bovine Viral Diarrhea Virus,”J. Virology75(19): 8987-8998, (2001).
Du Bois, et al., “Novel, Stereoselective Synthesis of 2-Amino Saccharides,”J. Am. Chem. Soc. 119:3179-3180, 1997.
Evans, B.E. et al., “Design of Nonpeptidal Ligands for a Peptide Receptor: Cholecystokinin Antagonists,”J. Med. Chem. 30:1229-1239 (1987).
Fletcher, M. D. and M.C. Campbell, “Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational Behavior,”Chem. Rev., 98:763-795, (1998).
Garro-Helion, et al., “Mild and Selective Palladium(0)-Catalyzed Deallylation of Allylic Amines. Allylamine and Diallylamine as Very Convenient Ammonia Equivalents for the Synthesis of Primary Amines,”J. Org. Chem., 58:6109-6113, (1993).
Golebiowski, A. and J. Jurczak, “α-Amino-β-hydroxy Acids in the Total Synthesis of Amino Sugars,”Synlett, pp. 241-245, (Apr., 1993).
Guillier et al., “Linkers and Cleavage Strategies in Solid-Phase Organic Syntheis and Combinatorial Chemistry,”Chem. Rev., 100:2091-2157, (2000).
Hanessian, S. et al., “Design and Synthesis of Conformationally Constrained Amino Acids as Versatile Scaffolds and Peptide Manners,”Tetrahedron, 53:12789-12854, (1997).
Hoyng, C.F. and A.D. Patel, “Aldehyde Components for Use in Four-Component Condensation (“4CC”) UGI Reaction Peptide Synthesis,”Tetrahedron Lett., 21:4795-4798, (1980).
Humphrey, J.M. and A.R. Chamberlin, “Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides,”Chem. Rev., 97:2243-2266, (1997).
König et al., “Synthesis of N-tert-Alkylglyoxylic Acid Amides,”Synthesis, pp. 1233-1234, (1993) [in German, English language abstract on 1stpage of article].
Marx et al., “Synthetic Design for Combinatorial Chemistry. Solution and Polymer-Supported Synthesis of Polycyclic Lactams by Intramolecular Cyclization of Azomethine Ylides,”J. Am. Chem. Soc., 119:6153-6167, (1997).
Mehta et al., “Structure-Activity Relationship of a New Class of Anti-Hepatitis B Virus Agents,”Antimicrobial Agents and Chemotherapy, 46(12);4004-4008 (2002).
Nicolaou et al., “Novel IBX-Mediated Process for the Synthesis of Amino Sugars and Libraries Thereof,”Angew. Chem. Int. Ed. Engl., 39:2525-2529, (2000).
Nicolaou, et al., “Lipoxins and Related Eicosanoids: Biosynthesis, Biological Properties, and Chemical Synthesis,”Angew. Chem. Int. Ed. Engl. 30:1100-1116, (1991).
Noyori, R. (Ed.), “Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification,” Chapter 5 inAsymmetrical Catalysis in Organic Synthesis, New York: John Wiley & Sons, Inc., pp. 255-297 (1994).
O'Donnell, Martin J. and J. Falmagne, “The Synthesis of Amino Acids via Organoboranes.”J. Chem. Soc. Chem. Commun., No. 17, pp. 1168-1169, (Sep. 1, 1985).
Petasis, N. A. and I.A. Zavialov, “The Boronic Acid Mannich Reaction: A New Method for the Synthesis of Geometrically Pure Allylamines.” Tetrahedron Letters, 34(4):583-386, (1993).
Petasis, N.A. and I.A. Zavialov, “A New and Practical Synthesis of α-Amino Acids from Alkenyl Boronic Acids,”J. Am. Chem. Soc., 119(2):445-446, (1997).
“Scope and Editorial Policy,”Organometallics, published by the American Chemical Society 21(1):13A, 14A (2002).
Serhan et al., “Novel Functional Sets of Lipid-derived Mediators with Antiinflammatory Actions Generated from Omega-3 Fatty Acids via Cyclooxygenase 2-Nonsteroidal Antiinfammatory Drugs and Transcellular Processing,”J. Exp. Med. 192:1197-1204, (2000).
Thompson, L.A. and J.A. Ellman, “Synthesis and Applications of Small Molecule Librari

Affiliated with

Also associated with

Rating

Nitrogen-containing heterocycles does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Nitrogen-containing heterocycles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Nitrogen-containing heterocycles will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3493655