Manufacture of cefalosporins and intermediates

Details Manufacture of cefalosporins and intermediates Manufacture of cefalosporins and intermediates

2005-06-14

2005-06-14

Berch, Mark L. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C540S227000

Reexamination Certificate

active

06906187

ABSTRACT:
There is described a process for the preparation of 3-disubstituted cepham-4-carboxylic acid derivatives of formula Iwherein R″ is 4-methoxybenzyl, X is the residue of a thioether and Z is a residue of a nucleophilic compound, such as 2-furoylthio, acetoxy or 1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-ylthio, by reaction of a functional derivative of α-(2-chloroacetamido)thiazol-4-yl-α-methoxyiminoacetic acid with 7β-amino-3-methylenecepham-4-carboxylic acid 4-methoxybenzyl ester, subsequent treatment of the obtained 4-methoxybenzyl 7β-[α-(2-chloroacetamido)thiazol-4-yl-α-methoxyimino]acetamido-3-methylenecepham-4-carboxylate with a S-chloromercaptan of formula X—S—Cl, such as methanesulfenyl chloride, and final treatment of the corresponding 4-methoxybenzyl 7β-[α-(2-chloroacetamido)thiazol-4-yl-α-methoxyimino]acetamido-3-thio-3-chloromethylcepham-4-carboxylate thus obtained of formula Vwherein R″ and X are as defined above, with a compound of formula M-Z, in which M is an alkaline metal or a hydrogen atom and Z is as defined above. These novel intermediates may be converted into the corresponding 3-cephem derivatives by oxidative cleavage of the mercaptan X—SH. By suitable deprotection, these 3-cephem derivatives afford cephalosporins such as ceftiofur, cefotaxime and ceftriaxone.

REFERENCES:
patent: 4327210 (1982-04-01), Montavon et al.
patent: 4622318 (1986-11-01), Takaya et al.

Affiliated with

Also associated with

Rating

Manufacture of cefalosporins and intermediates does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Manufacture of cefalosporins and intermediates, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Manufacture of cefalosporins and intermediates will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3519440