Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-05-01
2007-05-01
Shameem, Golam M. M. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S530000, C548S531000
Reexamination Certificate
active
11297954
ABSTRACT:
A process of preparing a compound of the formula (I)wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted alkyl, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof,which comprises reacting a compound of the formula (II)with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX),to form a compound of formula (XX)The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).
REFERENCES:
patent: 5985848 (1999-11-01), Furneaux et al.
patent: 6066722 (2000-05-01), Furneaux et al.
patent: 6583154 (2003-06-01), Norman et al.
patent: 6693193 (2004-02-01), Furneaux et al.
patent: 6803455 (2004-10-01), Furneaux et al.
patent: 7022852 (2006-04-01), Furneaux et al.
patent: WO 94/11534 (1994-05-01), None
patent: WO 99/19338 (1999-04-01), None
Braunheim, B.B. et al., “Prediction of Inhibitor Binding Free Energies by Quantum Neural Networks. Nucleoside Analogues Binding to Trypanosomal Nucleoside Hydrolase”, Biochemistry, Nov. 12, 1999, vol. 38, No. 49, 16076-16083.
Miles, R.W. et al., “Iminoribitol Transition State Analogue Inhibitors of Protozoan Nucleoside Hydrolases”. Biochemistry, Sep. 11, 1999, vol. 38, No. 40, 13147-13154.
Shi, W. et al., “The 2.0 Ang Structure of Malarial Purine Phosphoribosyltransferase in Complex with a Transition State Analogue Inhibitor”. Biochemistry, Jul. 13, 1999, vol. 38, No. 31, 9872-9880.
Li, C. et al., “Transition-State Analogs as Inhibitors of Human and Malarial Hypoxanthine-guanine Phosphoribosyltransferases”. Nat. Struct. Biol., 1999, vol. 6, No. 6, 582-587.
Miles, R. W. et al., “Purine Nucleoside Phosphorylase. Transition State Structure, Transition State Inhibitors and One-Third-The-Sites Reactivity”, Biomed. Health Res. Series, vol. 27 (Enzymatic Mechanisms, Frey & Northrop, eds), 32-47, 1999, IOS Press.
Furneaux, R.H. et al., “Improved Synthesis of 3H,5H-Pyrrolo[3,2,-d]pyrimidines”. J. Org. Chem, 1999, vol. 64, No. 22, 8411-8412.
Miles, R.W. et al., “One-Third-The-Sites Transition-State Inhibitors for Purine Nucleoside Phosphorolase”. Biochemistry, 1998, vol. 37, No. 24, 8615-8621.
Elliot, A.J. et al., “A Short, Facile Synthesis of 2-aminio-1,5-dihydro-4H-pyrrolo[3,2-d]-pyrimidin-4-one (9-deazaguanine)”. Tetrahedron Lett., 1996, vol. 37, No. 25, 4339-4340.
Brakta, M. et al., “Efficient Synthesis of 3H,5H-pyrrolo[3,2-d]pyrimidim-4-one”. J, Chem. Soc., Perkin Trans. 1, 1992, vol. 15, 1883-1884.
Taylor, E. C. et al., entitled “An Expeditious Synthesis of 2-Amino-4(3H)-oxo-5H-pyrrolo [3, 2-d] pyrimidine (9-Deazaguamine)” Tetrahedron Letters, vol. 34, No. 29, 1993, pp. 4595-4598.
Lim M-1 et al., entitled “A New Synthesis of Pyrrolo[3, 2-d]pyrimidines (“9-Deazapurines”) via 3-Amino-2-carboalkoxypyrroles” Journal of Organic Chemistry, vol. 44, No. 22, Oct. 26, 1979, pp. 3826-3829.
Lim, Mu-III et al., entitled “Synthesis of “9-deazaguanosine” and other new pyrrolo [3, 2-d] pyrimidine C-nucleosides” J. Org. Chem. (1983), 48(6), 780-8.
Elliott, Arthur J. et al., entitled “An Improved Synthesis of 7-substituted Pyrrolo [3,2-d]pyrimidines” Journal of Organic Chemistry (1997), 62(23), 8071-8075.
Ciller, Juan A. et al., “Ring Transformation of Isoxazoles into Furan and Pyran Derivatives” J. Chem. Soc. Perkin Trans. I, 1985, pp. 2581-2584.
Furneaux, R. H. et al., entitled “Synthesis of Transition State Inhibitors for N-Riboside Hydrolases and Transferases,” Tetrahedron, vol. 53, No. 8, pp. 2915-2930, 1997.
Furneaux Richard Hubert
Schramm Vern L.
Tyler Peter Charles
Albert Einstein College of Medicine of Yeshiva University
Amster Rothstein & Ebenstein LLP
Industrial Research Limited
Shameem Golam M. M.
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