Phosphinoamidite carboxylates and analogs thereof in the...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S026100, C536S027100, C536S028100

Reexamination Certificate

active

07745591

ABSTRACT:
Nucleoside phosphinoamidite carboxylates and analogs are provided that have the structure of formula (III)wherein A is hydrogen, hydroxyl, lower alkoxy, lower alkoxy-substituted lower alkoxy, halogen, SH, NH2, azide or DL wherein D is O, S or NH and L is a heteroatom-protecting group, unsubstituted hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; B is a nucleobase; and one of R11and R12is a blocking group and the other is (IV) or (VI)in which W, X, Y, Z, R1and n are as defined herein.

REFERENCES:
patent: 6121437 (2000-09-01), Guzaev et al.
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Supplementary European Search Report for EP 01 98 3160, dated Dec. 11, 2006 (4 pages).
Caruthers, H.H. et al. (1987) Synthesis of Oligonucleotides Using the Phosphramidite Method, in Bioactive Molecules, vol. 3, pp. 3-21, Elsevier, Amsterdam, NL.
Dellinger, D.J. et al. (2003) Solid-phase Chemical Synthesis of Phosphonoacetate and Thiophosphonoacetate Oligodeoxynucleotides, Journal of the American Chemical Society, 125(4):940-050.
Rudolph, M.J. et al. (1996) Phosphonoacetate Derivatives of Oligodeoxyribonucleotides, Nucleosides and Nucleotides, 15/11-12: 1725-1739.
Karlstedt, N.B. et al. (1976) Dialkoxyphosphines. III. Reaction of Dialkoxyphosphines with Alkali Metal Dialkylamines; Amido Esters of Hypophosphorous Acid; Abstract; STN Database Accession No. 86:5541; Khim Elementorg. Soedin. 172-5, Editors: Danilov, S.N.: publisher: “Nauka,” Leningr. Otd,, Leningrad, USSR; Coden: 33YRAV, 1976.
Marugg, J.E. et al. (1986) A New and Versatile Approach to the Preparation of Valuable Deoxynucleoside 3-Phosphite Intermediates, Tetrahedron Lett. 27/20:2271-2274.
Stepanov, I.A. et al. (1979) Synthesis of Phosphorus(III) Compounds Containing an Alpha-carboalkyoxymethyl Group; Abstract; STN Database Accession No. 92:129019, Zhurnal Obshscei Khimi (1979), 49(10), 2389; Coden: ZOKHA4; ISSN: 0044-460X, 1979.
Yamada, C. M. et al. (2006) Synthesis and Biochemical Evaluation of Phosphonoformate Oligodeoxyribonucleotides, Journal of the American Chemical Society 128(15):5251-5261.

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