Patent GB-1309588-A (GB)
Title: Antibiotics and a process for the manufacture thereof
Inventor: STEMPEL A
IPC: A23K20/195
Filed: 1970-08-06
Abstract: 1309588 Antibiotic X-537A derivatives F HOFFMANN-LA ROCHE & CO AG 6 Aug 1970 [18 Aug 1969] 37961/70 Heading C2A The invention comprises an antibiotic which is a derivative of the antibiotic designated X-537A and which has the Formula V wherein X represents a group of Formula I or of Formula II in which R 1  represents hydrogen, C 1 -C 7  alkyl, phenyl or phenyl substituted by halogen, nitro or C 1 -C 7  alkyl, R 2  represents hydrogen, C 1 -C 7  alkyl, C 1 -C 7  alkanoyl, a group of Formula III benzoyl or benzoyl substituted by halogen, nitro or C 1 -C 7  alkyl, R 3  represents hydrogen, halogen, nitro, amino, C 1 -C 7  alkanoylamino, C 1 -C 7  alkylamino, phenylazo or phenylazo substituted by halogen, nitro, C 1 -C 7  alkyl or C 1 -C 7  alkoxy, R 4  represents -OH, = O or = N-OH, with the proviso that at least one of R 1 , R 2  and R 3  is other than hydrogen or R 4  is other than = O and pharmaceutically acceptable salts of these compounds. The invention also comprises dehydration derivatives of compounds of Formula V in which X is a group of Formula I and R 4  is = O and pharmaceutically acceptable salts of these compounds. A process for the manufacture of compounds of Formula V comprises subjecting a compound of Formula IV or a pharmaceutically acceptable salt thereof, in any desired sequence, to one or more of the steps: (1) treatment with an esterifying agent to yield an ester group R 1 ; (2) treatment with a C 1 -C 7  alkylating agent to form a compound of Formula V in which R 1  and/or R 2  represents C 1 -C 7  alkyl; (3) treatment with an agent yielding C 1 -C 7  alkanoyl, a group of Formula III benzoyl, halobenzoyl, nitrobenzoyl or (C 1 -C 7  alkyl)-benzoyl group to form a compound of Formula V in which R 2  has the corresponding meaning; (4) treatment with a halogenating agent to form a compound of Formula V in which R 3  represents halogen; (5) treatment with a nitrating agent to form a compound of Formula V in which R 3  represents nitro; (6) treatment with a diazonium salt of aniline or an aniline substituted by halogen, nitro, C 1 -C 7  alkyl or C 1 -C 7  alkoxy to form a compound of Formula V in which R 3  represents phenylazo or phenylazo substituted by halogen, nitro, C 1 -C 7  alkyl or C 1 -C 7  alkoxy; (7) treatment with an acid addition salt of hydroxylamine to form a compound of Formula V in which R 4  represents hydroxyimino or reduction to form a compound of Formula V in which R 4  represents hydroxy or treatment with a dehydrating agent to form a corresponding dehydration product; whereupon, if desired, a nitro group present is reduced to an amino group or, in the presence of a C 1 -C 7  aldehyde, to a C 1 -C 7  alkylamino group; if desired, the so-formed amino group is C 1 -C 7  alkylated, C 1 -C 7  alkanoylated or converted into a diazo group by treatment with nitrous acid or C 1 -C 7  alkyl nitrite; and if desired, an acid of Formula V obtained is converted into a pharmaceutically acceptable salt thereof. Preparations which have coccidiostatic or antibacterial activity may contain one of the antibiotics of the invention in association with a compatible carrier material.