C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/104.1
C07D 501/34 (2006.01)
Patent
CA 1067068
A B S T R A C T This invention relates to a process for the preparation of an antibiotic compound of the formula Image (I) or a non-toxic derivative thereof, said compound being a syn isomer or existing as a mixture of syn and anti isomers containing at least 90% of the syn isomer, wherein (A) a compound of the formula Image (II) (wherein B is > S or > S ? O; R1 represents hydrogen or a carboxyl blocking group; and the dotted line bridging the 2-, 3- and 4- positions indicates that the compound is a ceph-2-em or ceph-3-em compound) or an acid addition salt or an N-silyl derivative thereof, is condensed with an acylating agent corresponding to an acid of formula Image (III) (wherein R2 is a carboxyl blocking group) or (B) a compound of the formula Image (IV) (wherein B and the dotted line are as defined above; and each R1 may in- dependently represent hydrogen or a carboxyl blocking group) is reacted with a carbamoylating agent serving to form a carbamoyloxymethyl or N-protected carbamoyloxymethyl group at the 3-position; whereafter, if necessary and/or desired in each instance, any of the following reactions (C), in any appropriate sequence, are carried out:- i) conversion of a .DELTA.2 isomer into the desired .DELTA.3 isomer, ii) reduction of a compound wherein B is > S ? O to form a compound wherein B is > S, and iii) removal of any carboxyl blocking and/or N-protecting groups; and finally (D) recovering the desired compound or a non-toxic derivative thereof, if necessary after separation of isomers. It also relates to the products of the process which are useful as broad spectrum antibiotics having particularly high activity against gram- negative microorganisms.
314938
Bradshaw Janice
Cook Martin C.
Gregory Gordon I.
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