Process for the cleavage of cephalosporin prodrug esters to 7-am

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

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

540228, C07D50104

Patent

active

054100429

ABSTRACT:
The present invention relates to a process for the preparation of 7-amino-3-methoxymethylceph-3-em-4-carboxylic acid (I) from 7-amino-3-methoxymethylceph-3-em-4-carboxylic acid esters (II) or their salts by ester cleavage.
The process comprises treating the compound II with formic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid or a mixture of two of these acids in each case.

REFERENCES:
patent: 4098888 (1978-07-01), Ochiai et al.
patent: 4203899 (1980-05-01), Ochiai et al.
patent: 4205180 (1980-05-01), Ochiai et al.
patent: 4264595 (1981-04-01), Numata et al.
patent: 4278793 (1981-07-01), Durckheimer et al.
patent: 4283396 (1981-08-01), Heymes et al.
patent: 4298606 (1981-11-01), Ochiai et al.
patent: 4355160 (1982-10-01), Ochiai et al.
patent: 4409215 (1983-10-01), Takaya et al.
patent: 4462999 (1984-07-01), Takaya et al.
patent: 4483855 (1984-11-01), Nakao et al.
patent: 4486425 (1984-12-01), Nakao et al.
patent: 4514565 (1985-04-01), Ochiai et al.
patent: 4668783 (1987-05-01), Ochiai et al.
patent: 4904652 (1990-02-01), Takaya et al.
patent: 4912212 (1990-03-01), Ochiai et al.
patent: 4973684 (1990-11-01), Ochiai et al.
patent: 4992431 (1991-03-01), Heymes et al.
patent: 5026695 (1991-06-01), Takaya et al.
patent: 5063224 (1991-11-01), Mosher et al.
patent: 5100887 (1992-03-01), Adam et al.
Kamiya, T., et al., "Tentative Protection of Carboxyl Groups," Chem. Abstracts 82 (1975), p. 517, No. 112093g.
Kamiya, T., et al., "Carboxy Group-Containing Compounds," Chem. Abstracts 82 (1975), p. 501, No. 3138p.
Kametani, T., et al., "The Deblocking of Cephalosporin Benzhydryl Esters With Formic Acid," Chem. Abstracts 98 (1983), p. 625, No. 179032k.
Webber, J. A., et al., "Chemistry of Cephalosporin Antibiotics, XVII. Functionalization of Deacetoxycephalosporin. The Conversion of Penicillin into Cephalosporin," J. Am. Chem. Soc. 91 (20), p. 5974 (1969).
Ogliaruso, M. A., et al., Synthesis of Carboxylic Acids, Esters, and Their Derivatives; J. Wiley and Sons 1991, pp. 229-230.
Chandrasekaran, S., et al., "Synthesis of Substituted .beta.-lactams by Addition of Nitromethane to 6-Oxopenicillanates and 7-Oxocephalosporanates," J. Org. Chem. 42 (24), 3972 (1977).
S. Torii et al., J. Org. Chem. 56:3633 (1991).
H. Kamachi et al., J. Antibiotics 41(11):1602 (1988).
K. Fujimoto et al., J. Antibiotics 40(3):370 (1987).
T. Nishimura et al., J. Antibiotics 40(1):81 (1987).
E. Defossa et al., Abstract No. 187, Cefdaloxime Pentexil Tosilate (HR916K): a Diastereomerically Pure Novel Oral Cephalosporinester: Synthesis and Antibacterial Activity In Vivo (Oct. 11-14, 1991).
D. Isert et al., Abstract No. 188, Cefdaloxime Pentexil Tosilate (HR916K): a Diastereomerically Pure Novel Oral Cephalosporinester with Outstanding Absorption Characteristics (Oct. 11-14, 1991).
"Cefpodoxime Proxetil", Drugs of the Future, 14(1):73-74 (1989).
"SCE-2174", Drugs of the Future, 13(3):231-233 (1988).
"Cefuroxime Axetil", Drugs of the Future, 10(2):112-113 (1985).
"Antibiotic Activity of CL 118,673, a New Oral Cephalosporin", N. A. Kuck et al., Recent Advances In Chemotherapy, Proceedings of the 14th Int'l. Congress of Chemotherpay, Antimicrobial Section 2, pp. 1137-1138 (1985).
Improved Synthesis of an Ester-Type Prodrug, 1-Acetoxyethyl 7-[(Z)-2-(2-Aminothiazol-4-yl)-2-Hydroxyiminoacetamido]-3-[(Z)-1-Propenyl] -3-Cephem-4-Carboxylate (BMY-28271), Hajime Kamachi et al., The Journal of Antibiotics, vol. XLIII(12):1564-1572 (1990).
"Beta-Lactam Compounds", Chemical Abstracts, 102:220658k (1985).
"Cephalosporin derivatives", Chemical Abstracts, 102:220657j (1985).

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

Process for the cleavage of cephalosporin prodrug esters to 7-am does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the cleavage of cephalosporin prodrug esters to 7-am, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the cleavage of cephalosporin prodrug esters to 7-am will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1568692

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