Intermediate of carbapenem antibiotics and process for the...

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

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C544S071000, C544S097000

Reexamination Certificate

active

06858727

ABSTRACT:
There is disclosed an azetidinone compound of the formula (I):wherein R is hydrogen, or a hydroxy protecting group, R1and R2are each independently alkyl of 1-15 carbon atoms, benzyl or cyclized together with the carbon atom to which they are attached to form a 5 or 6-membered cyclic hydrocarbon or a heterocyclic radical having one or two hetero ring atoms, said hetero ring atoms being selected from the group consisting of O and S; R3is lower alkyl or —COO(lower alkyl) R4is phenyl, or phenyl substituted with halogen, lower alkoxy or nitro which is useful as a synthetic intermediate to the 1′β-methylcarbapenem-type antibacterial agent.

REFERENCES:
patent: 5442055 (1995-08-01), Iwasaki et al.
patent: 5631363 (1997-05-01), Iwasaki et al.
patent: 5847115 (1998-12-01), Iwasaki et al.
patent: 6011150 (2000-01-01), Iwasaki et al.
patent: 6340751 (2002-01-01), Saito et al.
patent: 0 126 587 (1984-05-01), None
patent: 62-252786 (1987-11-01), None
patent: 63-188662 (1988-08-01), None
patent: 64-025779 (1989-01-01), None
patent: 4-279588 (1992-05-01), None
patent: 07-082248 (1995-03-01), None
patent: 07-082249 (1995-03-01), None
Fuentes, L.M. et al., “Lewis Acid Mediated Condensation of Chiral Imide Enolates: A General Approach to the Synthesis of Chiral Carbapenem Precursors,” 108 J. Am. Chem. Soc. pp. 4675-4676 (1986).
Nagao, Yoshimitsu et al., “Highly Diastereoselective Alkylation onto 4-Acetoxy-2azetidinones Employing Tin(II)Enolates of C4-Chiral 3-Acyl-1,3-thiezolidine-2-thiones,” 108 J. Am. Chem. Soc. pp. 4673-4675 (1986).
Shibata, Tomoyuki et al., “Synthetic Studies of 1-β-Methylcarbapenem Antibiotics,” The Journal of Antibiotics pp. 374-381 (1989).
Remuzon, Phillippe et al., “Studies Toward the Stereocontrolled Synthesis of a Key Azetidinone-Acid Intermediate i the Preparation of a New Carbapenem,” 51(35) Tetrahedron pp. 9657-9670 (1995) Great Britain.
Deziel, Robert et al., “Simple and Highly Diastereoselective Synthesis of a 1β-Methylcarbapenem Key Intermediate Involving Divalent Tin Enolates,” 27(47) Tetrahedron Letters pp. 5687-5690 (1986) Great Britain.
Ito, Yoshio, et al.,Highly Stereocontrolled Synthesis of the 1β-Methylcarbapenem Key Intermediate by the Reformatsky Reaction of 3-(2-Bromopropionyl)-2-Oxazolidone Derivatives with a 4-Acetoxy-2-Azetidinone1) 47(16/17) Tetrahedron pp. 2801-2820 (1991) Great Britain.
Ito, Yoshio, et al., “A Highly Stereoselective Synthesis of a Key Intermediate of 1β-Methylcarbapenems Employing the Reformatsky Reaction of 3-(2Bromopropionyl)-2-Oxazolidone Derivatives,” 28(52) Tetrahedron Letters pp. 6625-6628 (1987) Great Britain.
Berks, Andrew H., “Preparation of Two Pivotal Intermediates for the Synthesis of 1β-Methyl Carbapenem Antibiotics,” 52(2) Tetrahedron pp. 331-375 (1996) Great Britain.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Intermediate of carbapenem antibiotics and process for the... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Intermediate of carbapenem antibiotics and process for the..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intermediate of carbapenem antibiotics and process for the... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3457035

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.