2-vinylpenams and process
OwnerJack E. Baldwininventor
Life of this patent
Estimating the term…
Abstract
6.beta.-(L-.alpha.-Aminoadipoyl)-2.alpha.-vinyl-2.beta.-methylpenam-3-carbo xylic acid is provided in an enzymatic process converting .delta.-(L-.alpha.-aminoadipoyl)-L-cysteinyl-D-.gamma.,.delta.-didehydrois oleucine with isopenicillin N synthetase. The 2.alpha.-vinylpenam product is converted by known methods to the 6.beta.-amino-2.alpha.-vinyl-2.beta.-methylpenam-3-carboxylic acid nucleus and the latter is N-acylated to provide corresponding 6.beta.-acylaminopenams.
Claims14
The process for preparing a compound of the formula ##STR22## which comprises contacting in an aqueous medium at a temperature between about 20.degree. C. and about 40.degree. C. and at a pH of between about 6 and about 9 in the presence of ferrous ion and ascorbic acid a tripeptide of the formula ##STR23## with isopenicillin N synthetase.
A compound of the formula ##STR24## wherein R is .alpha.-aminoadipoyl or an acyl group of the formula ##STR25## wherein R.sup.1 is a phenyl group of the formula ##STR26## wherein a and b independently are hydrogen, hydroxy, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, amino, C.sub.1 -C.sub.4 alkylsulfonylamino, carboxy, carbamoyl, carboxymethyl, hydroxymethyl, aminomethyl or trifluoromethyl;
- Z is O or S, Y is a straight or branched chain divalent C.sub.1 -C.sub.4 alkylene radical and m and n are 0 or 1;
- or R.sup.1 is cyclohexenyl or cyclohexadienyl;
- or R is a heteroalkanoyl group of the formula ##STR27## wherein R.sup.2 is thienyl, furyl, benzothienyl, benzofuryl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl and the aforesaid heterocycles substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, amino or halogen;
- an isoxazolyl group of the formula ##STR28## wherein d and d' independently are C.sub.1 -C.sub.4 alkyl, phenyl, halophenyl or hydroxyphenyl;
- and Y and n have the same meaning as defined above;
- or R is an acyl group ##STR29## wherein R.sup.3 is R.sup.1 or R.sup.2 as defined above and Q is hydroxy, C.sub.1 -C.sub.4 alkanoyloxy, carboxy, sulfo, amino or a substituted amino group of the formula ##STR30## wherein R.sup.3' is hydrogen, C.sub.1 -C.sub.4 alkanoyl or C.sub.1 -C.sub.4 alkylsulfonyl and R.sup.3" is C.sub.1 -C.sub.4 alkyl or benzyl;
- or R is a cyclic acyl group of the formula ##STR31## wherein R.sup.1 has the same meanings as defined above and alk and alk' independently are C.sub.1 -C.sub.3 alkyl;
- or R is an oximino-substituted acyl group of the formula ##STR32## wherein R.sup.4 is R.sup.1 or R.sup.2 as defined above and R.sup.4' is a straight or branched chain C.sub.1 -C.sub.6 alkyl radical or substituted C.sub.1 -C.sub.6 alkyl radical substituted by hydroxy, amino, carboxy, carbamoyl, N,N-di(C.sub.1 -C.sub.4 alkyl)carbamoyl or cyano;
- R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or formamido;
- and the pharmaceutically acceptable, non-toxic salts thereof.
A compound of the formula ##STR40## and the carboxy-protecting esters and salts thereof.
Dependencies are inferred from the claim text.