Process for the manufacture of 1-sulpho-2-oxoazetidine derivativ

Details Process for the manufacture of 1-sulpho-2-oxoazetidine derivativ Process for the manufacture of 1-sulpho-2-oxoazetidine derivativ

1989-02-28

1990-08-14

Gerstl, Robert

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548233, 548337, 548378, 548194, C07D21373, C07D23112, C07D23346, C07D26348

Patent

active

049488988

ABSTRACT:
The manufacture of 1-sulpho-2-oxazetidine derivatives of the formula ##STR1## in which Het is an optionally amino-substituted, 5- or 6-membered, aromatic heterocycle containing 1 or 2 nitrogen atoms and optionally also an oxygen or sulphur atom, R.sup.1 is hydrogen, lower alkyl, phenyl-lower alkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkenyl-lower alkyl, lower alkoxycarbonyl-lower alkyl, phenyl-lower-alkoxycarbonyl-lower alkyl, nitrophenyl-lower-alkoxycarbonyl-lower alkyl or carboxy-lower alkyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxycarbonyl, lower alkanoyloxy-lower alkyl, lower alkoxycarbonyl-lower alkenyl, hydroxyiminomethyl, lower alkoxyiminomethyl, carbamoyl, carbamoyl-lower alkenyl or carbamoyloxy-lower alkyl, the group .dbd.NOR.sup.1 being present at least partially in the syn-form,
in racemic form or in the form of the 3S-enantiomer, and of readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, by acylating a compound of the formula ##STR2## in which R.sup.20 equals R.sup.2 or can also represent a 2,2-dimethyl-1,3-dioxolan-4-yl group and R.sup.3 is hydrogen or sulpho,
or a salt thereof with a thioester of the formula ##STR3## in which Het is as above and R.sup.10 has any of the values of R.sup.1 except carboxy-lower alkyl, and can also represent a tri-lower alkyl-silyl-lower-alkoxycarbonyl-lower alkyl group or a carboxy-lower alkyl group converted into a readily hydrolyzable ester group, and the group .dbd.NOR.sup.10 is present at least partially in the syn-form,
and carrying out subsequent steps (N-sulphonation, conversion of R.sup.20 into R.sup.2, R.sup.10 into R.sup.1), some of which are optional.
The invention also provides certain novel products of formula I and benzthiazolyl thioesters of formula III per se and the preparation of the benzthiazolyl thioesters by esterifying corresponding carboxylic acids. Finally, the invention provides a process for the preparation of carboxylic acids in which R.sup.1 is t-alkoxycarbonylmethyl.
The compounds of formula I have antimicrobial activity.

REFERENCES:
patent: 4304718 (1981-12-01), Kamiya
patent: 4385181 (1983-05-01), Farge
patent: 4572801 (1986-02-01), Matsuo

Affiliated with

Also associated with

Rating

Process for the manufacture of 1-sulpho-2-oxoazetidine derivativ 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 manufacture of 1-sulpho-2-oxoazetidine derivativ, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the manufacture of 1-sulpho-2-oxoazetidine derivativ will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-464069