Processes for the preparation of cephalosporin derivatives

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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07622577

ABSTRACT:
Provided is a process for preparing a compound of formula 1 or its salt, which comprises reacting a compound represented by the following formula 4 with acetaldehyde in a mixed solvent comprising water, isopropanol, and methylenechloride in a volume ratio of 1:3-6:11-14 in the presence of a first base to stereospecifically prepare a compound represented by the following formula 3′; andreacting the compound of the formula 3′ with an anhydrous compound represented by the following formula 2 in the presence of a second base:wherein R1is a hydrogen or an amino protecting group, R2is a hydrogen or a carboxyl protecting group, and R3is a hydrogen or an amino protecting group consisting of phenylacetyl group,wherein when R3is a phenylacetyl group, R2is not a hydrogen in formula 3′; andwherein, when at least one of R2and R3is a protecting group, all such protecting groups are removed from formula 3′, thereby producing a compound represented by formula 6 prior to reacting it with the compound of formula 2.

REFERENCES:
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patent: 6903211 (2005-06-01), Deshpande et al.
patent: 7112672 (2006-09-01), Lee et al.
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patent: 03011871 (2003-02-01), None
Naito et al., “Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds,” J. Antibiotics, vol. 40, No. 7, 1987, pp. 991-1005.
deVroom et. al., “Synthesis of 3-alkenylcephalosporins using an epoxide mediated wittig reaction,” Recl. Trav. Chim. Pays-Bas, vol. 113, 1994, pp. 305-306.
Curini et al., “An improved procedure for the preparation of a 3-(alkenyl) cephem derivative,” Gazzetta Chimica Italiana, vol. 127, 1997, pp. 195-196.
Indian Office Action issued in IN 2320/DELNP/2006 dated Mar. 17, 2009, 6 pages.

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