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US 4,053,469 AGranted
Intermediates for the preparation of 7-acylamino-3-oxyiminomethyl-3-cephem-4-carboxylic acids
AssigneeShionogi & Co., Ltd.
InventorsMitsuru Yoshioka, Masayuki Murakami, Yuji Sendo
Life of this patent
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Abstract
An antibacterial 7-protected amino-3-oxyiminomethyl-3-cephem-4-carboxylic acid is prepared by the reaction of a 7-protected amino-3-formyl-3-cephem-4-carboxylic acid or its reactive derivatives with a hydroxylamine compound or its reactive derivatives, the process being more suitable for large scale production when coupled with fermentative production of a 3-hydroxymethyl-3-cephem-4-carboxylic acid followed by its direct oxidation.
Claims2
A compound selected from the group consisting of (1) a compound of the formula:
- ##STR85## wherein Y is hydrogen or methoxy
- R is hydrogen or methyl;
- R' is a member selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl, tertiary butyl, n-pentyl, secondary pentyl, neopentyl, n-hexyl, 2-chloroethyl, 2-bromoethyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 4-bromobutyl, 2-chlorohexyl, methoxymethyl, methoxyethyl, methoxypropyl, ethoxyethyl, norbornyloxymethyl, propoxypropyl, methylthiomethyl, methylthioethyl, methylthiopropyl, N,N-dimethylaminoethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylcyclohexyl, benzyl, 4-nitrobenzyl, 4-methoxybenzyl, phenyl, tolyl, xylyl, mesityl, 4-ethylphenyl, .alpha.-naphthyl, .beta.-naphthyl, vinyl, allyl, hexenyl, cyclohexenyl, ethinyl, propargyl, carboxymethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, hexyloxycarbonylmethyl, butoxycarbonylmethyl, carbamoylmethyl, .alpha.-carboxyethyl, .alpha.-carbethoxyethyl, .alpha.-carbamoylethyl, and .alpha.-(N-methylcarbamoyl) ethyl;
- and
- R" is a member selected from the group consisting of allyl, ethinyl, propargyl, benzyl, p-methoxybenzyl, carbamoylmethyl, and N-methylcarbamoyl, and (2) a derivative thereof bearing a protective grouping at the carboxyl group, said grouping being a member selected from the group consisting of a haloalkyl ester, a tertiary alkyl ester of 4-6 carbon atoms, a tertiary alkenyl ester of 5-7 carbon atoms, a tertiary alkynyl ester of 5-7 carbon atoms, benzyl ester, methoxybenzyl ester, nitrobenzyl ester, 3,5-di-(tertiary butyl)-4-hydroxybenzyl ester, acetoxymethyl ester, pivaloyloxy-methyl ester, benzhydryl ester, phenacyl ester, trimethylsilyl ester, succinimidomethyl ester, phthalimidomethyl ester, and the 1,2-di-isopropylhydrazide.
2 more elements
Dependencies are inferred from the claim text.