Isopenicillins

Claim 2

A compound of the formula ##STR7## wherein R is acylamino, azido, or amino; acyl is a pharmaceutically acceptable acyl group known to be useful to impart antibacterial activity when used as a substituent on the 7 or 6 position amino group of cephalosporins or penicillins; and M is hydrogen, a pharmaceutically acceptable cation or a removable carboxylic acid protecting ester.

Claim 3

A compound as claimed in claim 1 where R is acylamino.

Claim 4

A compound as claimed in claim 2 where ##STR8## X is thienyl, furyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, phenyl or phenyl substituted with one or two substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, hydroxymethyl, halo, nitro, mercapto, lower alkylthio, trifluoromethyl, ureido, formamido, and carboxymethylamino; A is hydroxy, formyloxy, carboxy, sulfo or (when the α-hydrogen is absent) methoxyimino or oximino; Y is cyano, azido, phenyl, phenoxy, or a heterocyclic ring selected from the group consisting of thienyl, furyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, and pyrimidyl, each heterocyclic ring being unsubstituted or substituted with one or two substituents selected from the group consisting of lower alkyl, halo, hydroxy, nitro, lower alkoxy, phenyl and phenylalkyl; Z is phenyl, pyridyl, lower alkyl, trifluoromethyl, trifluoromethyl, or cyanomethyl; n is 0, 1 or 2; and M is hydrogen or a pharmaceutically acceptable cation.

Claim 5

A compound as claimed in claim 3 where acyl is mandeloly, α-formyloxyphenylacetyl, trifluoromethylmercaptoacetyl, methylmercaptoacetyl, methylsulfonylacetyl, 2,2,2-trifluoroethylsulfinylacetyl, cyanoacetyl, cyanomethylmercaptoacetyl, α-carboxy-2-thienylacetyl, α-carboxy-3-thienylacetyl, α-carboxyphenylacetyl, α-sulfophenylacetyl, 2-thienylacetyl, 1-tetrazolylacetyl, phenoxyacetyl, phenylacetyl, 4-pyridylmercaptoacetyl, α-syn-methoxyimino(2-furyl)acetyl, or α-oximinophenylacetyl.

Claim 6

A compound as claimed in claim 4 being the compound 6β-phenoxyacetamido-7-oxo-3-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylic acid and its cyclohexylamine, sodium or potassium salt.

Claim 7

A compound as claimed in claim 4 being the compound 6β-(2-thienylacetamido)-7-oxo-3-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylic acid and its cyclohexylamine, sodium or potassium salt.

Claim 8

A compound as claimed in claim 1 where R is amino and M is a removable carboxylic acid protecting ester.

Claim 9

A compound as claimed in claim 7 where R is amino and M is methyl, benzyl or benzhydryl.

Claim 10

A compound as claimed in claim 8 being the compound benzyl 6β-amino-7-oxo-3-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate.

Claim 11

A compound as claimed in claim 8 being the compound benzhydryl 6β-amino-7-oxo-3-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylate.

Claim 12

A compound as claimed in claim 1 where R is azido and M is hydrogen or a removable carboxylic acid protecting ester.

Claim 13

A compound as claimed in claim 11 being the compound 6β-azido-7-oxo-3-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

Claim 14

A compound as claimed in claim 12 being the benzhydryl ester.

Claim 15

A compound as claimed in claim 12 being the benzyl ester.

Claim 16

A process for preparing compounds of claim 1 where R is acylamino or azido comprising treating a compound of the formula ##STR9## where R is acylamino or azido; acyl is a pharmaceutically acceptable acyl group known to be useful to impart antibacterial activity when used as a substituent on the 7 or 6 position amino group of cephalosporins or penicillins; X is halogen and M is hydrogen, alkali metal cation or a removable carboxylic acid protecting group, with a cyclohexylamine.