Synthesis of macrocyclic tetraamido compounds and new metal...

Details Synthesis of macrocyclic tetraamido compounds and new metal... Synthesis of macrocyclic tetraamido compounds and new metal...

2006-06-13

2006-06-13

Wilson, James O. (Department: 1624)

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C540S473000, C540S474000, C540S545000

Reexamination Certificate

active

07060818

ABSTRACT:
An improved method of synthesizing a macrocyclic tetraamido compound includes protecting the amino portion of an amino carboxylic acid to form a protected amino carboxylic acid; exposing the protected amino carboxylic acid to a first solvent, preferably a hydrocarbon solvent, such as toluene or 1,2-dichloroethane, dichloromethane, dibromomethane and 1,2-dibromoethane. The carboxylic acid portion of the protected amino carboxylic acid is then converted to an activated carboxylic acid by one of esterification or acid halide formation, to form a protected amino activated carboxylic acid derivative. The protected amino activated carboxylic acid derivative is reacted with a diamine in the presence of a second solvent, such as THF or ,2-dichloroethane, dichloromethane, dibromomethane and 1,2-dibromoethane, to form a protected diamide diamine intermediate. Following deprotection, the diamide diamine intermediate is reacted with an activated diacid, such as an activated malonate, oxalate or succinate derivative to form the macrocyclic tetraamido compound. The macrocyclic tetraamido compound may further be complexed with a transition metal.

REFERENCES:
patent: 4517122 (1985-05-01), Tomalia et al.
patent: 4577042 (1986-03-01), Collins et al.
patent: 4758682 (1988-07-01), Collins et al.
patent: 4923985 (1990-05-01), Gansow et al.
patent: 5189160 (1993-02-01), Memeger, Jr.
patent: 5247075 (1993-09-01), Parker et al.
patent: 5298618 (1994-03-01), Speranza et al.
patent: 5445755 (1995-08-01), Convents et al.
patent: 5474576 (1995-12-01), Thoen et al.
patent: 5785886 (1998-07-01), Kerschner et al.
patent: 5847120 (1998-12-01), Collins et al.
patent: 5853428 (1998-12-01), Collins et al.
patent: 5876625 (1999-03-01), Collins et al.
patent: 6051704 (2000-04-01), Gordon-Wylie et al.
patent: 6054580 (2000-04-01), Collins et al.
patent: 6099586 (2000-08-01), Collins et al.
patent: 6127536 (2000-10-01), Deline et al.
patent: 6136223 (2000-10-01), Collins et al.
patent: 6241779 (2001-06-01), Collins et al.
patent: 6297400 (2001-10-01), Deline et al.
patent: 6384279 (2002-05-01), Deline et al.
patent: 2002/0134965 (2002-09-01), Danjo
patent: 2003/0168630 (2003-09-01), Carlina et al.
patent: WO 94/12621 (1994-06-01), None
patent: WO 94/21777 (1994-09-01), None
patent: WO 95/31526 (1995-11-01), None
patent: WO 97/29174 (1997-08-01), None
patent: WO 97/48787 (1997-12-01), None
patent: WO 98/39405 (1998-09-01), None
patent: WO 02/16330 (2002-02-01), None
patent: WO 03/014277 (2003-02-01), None
patent: WO 03/014279 (2003-02-01), None
patent: WO 03/014280 (2003-02-01), None
McGraw-Hill-Dictionary of Chemical Terms, © 1984 by McGraw-Hill, Inc., p. 251.
Grant & Hackh's Chemical Dictionary, 5th ed. © 1987 by McGraw-Hill, Inc. p. 347.
Hawley's Condensed Chemical Dictionary, © 1997 by Van Nostrand Reinhold, pp. 587 and 687.
Okuno et al, “A Convenient Method for the Synthesis of Macrocyclic Tetra-amides by Double Condensation Reaction” J. Chem Soc. Perkin Trans. I, vol. 5, pp. 1115-1118 (1984).
The Merck Index, 13thed., Merck & Co., Inc. Whitehouse Station, NJ USA © 2001. p. 1791.
Dale et al, “The Chemical Development of the Commercial Route to Sildenafil: A Case History” Organic Process Research and Development, vol. 4, pp. 17-200 (2000).
Al-Hassan, S. S. et al., Specific Inhibitors in Vitamin Biosynthesis. Part 7. Synthesis of Blocked 7,8-Dihydropteridines via α-Amino Ketones, J. Chem. Soc., Perkin Trans. 1 1985, pp. 1645-1659.
Bradshaw, J. S. et al., Aza-Crown Macrocycles, Chap IV, p. 146, John Wiley & Sons Inc., 1993.
Buschmann, J. et al., The Structures of Difluorodiisocyanatomethane, CF2(NCO)2: X-ray Crystallography, Gas Electron Diffraction, and Quantum Chemical Calculations, Phys. Chem. A 2000, 104, pp. 7123-7128.
Bushby, R. J. et al., The Introduction of Alkylidene Substituents into the 4-Position of the 3,3,5,5-Tetramethyl- Δ -pyrazoline Nucleus by the Thioketone plus Diazoalkane Reaction: Synthesis of Tetrasubstituted Episulphides and Alkenes, J. Chem. Soc., Perkin Trans. 1, pp. 2401-2408, 1979.
Collins, T. J., Designing Ligands for Oxidizing Complexes, Department of Chemistry, Carnegie Mellon University, Accounts of Chemical Research, 1994, 27, pp. 279-285.
Drake, N. L. et al. Synthetic Antimarlarials, Some Derivatives of 8-Aminoquinoline, Laboratories of the University of Maryland, vol. 68, Aug. 1946, pp. 1536-1543.
Fletcher, G. A. et al., A List of Amino-Acid Derivatives Which Are Useful in Peptide Synthesis, Int. J. Peptide Protein Res. 4, 1972, pp. 347-371.
Greene, T. W., Protective Groups in Organic Synthesis, Chap. V, pp. 154-192, Chap. VII, pp. 218-287, Harvard University, John Wiley & Sons, 1981.
Kozmin, A. S. et al., Opening of the Three-Membered Ring of Derivatives of Cyclopropane-1, 1-Dicarboxylic Acid in the Reaction with Hydazine Hydrate, trans. from Zhumal Organicheskoi Khimii, vol. 7, No. 10, p. 2224, Oct., 1971, Journal of Organic Chemistry of U.S.S.R., pp. 2309-2310.
Keinan, E. et al., Diiodosilane. 3. Direct Synthesis of Acyl Iodides from Carboxylic Acids, Esters, Lactones, Acyl Chlorides, and Anhydrides, J. Org. Chem. 1990, 55, pp. 3922-3926.
Krapcho, A. P. et al., α—Carbalkoxylations of Carboxylic Acids, A General Synthetic Route to Monoesters of Malonic Acids, Tetrahedron Letters No. 32, pp. 2721-2723, 1974.
Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, Wiley-VCH, New York, 2nded., 1999, pp. 1941-1954.
Nakamura, M. et al., Fluorimetric Determination of Aromatic Aldehydes With 4,5-Dimethoxyl-1,2-Diaminobenzene, Analytica Chimica Acta, 134, 1982, pp. 39-45.

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