C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/104.1
C07D 501/34 (2006.01)
Patent
CA 1067067
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 exist- ing 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 ? 0; 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 carbamoyloxy-methyl or N-protected carbamoyloxy-methyl group at the 3-position; whereafter, if necessary and/or desired in each instance, any of the following reactions (C), in any approp- riate 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 this process which are broad spectrum antibiotics having particularly high activity against gram-negative micro- organisms.
314937
Bradshaw Janice
Cook Martin C.
Gregory Gordon I.
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