3-hydrazino-2,5-dioxopyrrolidine-3-carboxylates, process for...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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08003808

ABSTRACT:
The present invention provides 3-hydrazino-2,5-dioxopyrrolidine-3-carboxylates of the formula (I):wherein R1is a C1-6alkyl group, etc., R2is a hydrogen atom or a COOR3group, wherein R3is a tert-C4-6alkyl group, a 2,2,2-trichloroethyl group or a benzyl group in which the benzene ring moiety may be optionally substituted by one or two atoms or groups independently selected from the group consisting of a halogen atom, a C1-4alkyl group, a C1-4alkoxy group, a cyano group and a nitro group, and a salt thereof, which are useful as a novel intermediate for preparing tetrahydropyrrolo[1,2-a]pyrazin-4-spiro-3′-pyrrolidine derivatives such as Ranirestat being promising therapeutic agents for diabetic complications in a short process and in an economically advantageous and safe manner, and the process for preparing the same.

REFERENCES:
patent: 5258382 (1993-11-01), Negoro et al.
patent: 5-186472 (1993-07-01), None
patent: 6-192222 (1994-07-01), None
Negoro et al. (J. Med. Chem., 41 (1998), 4118-4129).
International Search Report dated Jul. 31, 2007 in the International (PCT) Application PCT/JP2007/061887 of which the present application is the U.S. National Stage.
English translation of PCT Written Opinion dated Jan. 29, 2009 in the International (PCT) Application PCT/JP2007/061887 of which the present application is the U.S. National Stage.
Toshiyuki Negoro et al., “Novel, Highly Potent Aldose Reductase Inhibitors: (R)-(−)-2-(4-Bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3′-pyrrolidine-1,2′,3,5′-tetrone (AS-3201) and Its Congeners”, Journal of Medicinal Chemistry, vol. 41, pp. 4118-4129, 1998.
Mashiko et al., “En Route to an Efficient Catalytic Asymmetric Synthesis of AS-3201”, J. Am. Chem. Soc. (2007) vol. 129, pp. 11342-11343.

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