Alkenyl and alkinylureido cephalosporins

Claim 2

A compound of the formula: ##STR343## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl) silyl, trihaloethyl, an alkali metal ion, and alkaline earth metal ion, an alkaline earth metal ion, dibenzylamine, N,N-dibenzylethylenediamine, methylamine, triethylamino, N-ethylpiperidine or ##STR344## R 2 is lower alkenyl or lower alkinyl; R 3 is hydrogen or lower alkyl; R 4 is phenyl, phenyl-lower alkyl, substituted phenyl or phenyl-lower alkyl wherein said phenyl substituent is one or two members selected from the group consisting of halogen, lower alky of 1 to 4 carbons lower alkoxy of 1 to 4 carbons, and hydroxy, or a substituted or unsubstituted heterocyclic selected from the group consisting of 2-thienyl, 3-thienyl, 2-furyl, and 3-furyl wherein said heterocyclic substituent is attached at an available carbon atom and is halogen or lower alkyl of 1 to 4 carbons; R 5 is hydrogen or lower alkyl; R 6 is lower alkyl; and X is a heterothio group selected from the group consisting of ##STR345## wherein R 7 is hydrogen or lower alkyl of 1 to 4 carbons and R 8 is hydrogen, lower alkyl of 1 4 carbons, methoxy, hydroxy,or halogen.

Claim 3

The compound of claim 1 wherein R is hydrogen straight or branched chain alkyl of 1 to 4 carbons, benzyl, phenethyl, diphenylmethyl, trimethylsilyl, 2,2,2-trichloroethyl, an alkali metal ion, and alkaline earth metal ion, dibenzylamine, N,N-dibenzylethylenediamine, methylamine, triethylamino, N-ethylpiperidine, or ##STR346## R 2 is lower alkenyl or lower alkinyl wherein said alkenyl or alkinyl is straight or branched chain of 2 to 8 carbons having one double or triple bond; R 3 is hydrogen or lower alkyl wherein lower alkyl is straight or branched chain of 1 to 8 carbons; R 4 is phenyl, benzyl, phenethyl, substituted phenyl, benzyl or phenethyl wherein said substituent is on the phenyl ring and is one or two members selected from the group consisting of chloro, bromo, methyl, ethyl, methoxy, ethoxy and hydroxy, or a substituted or unsubstituted heterocyclic selected from the group consisting of 2-thienyl, 3-thienyl, 2-furyl, and 3-furyl wherein said heterocyclic substituent is attached at an available carbon atom and is chloro, bromo, methyl, or ethyl, R 5 is hydrogen or straight or branched chain alkyl of 1 to 4 carbons; R 6 is straight or branched chain alkyl of 1 to 4 carbons; and X is a heterothio group selected from the group consisting of ##STR347## wherein R 7 is hydrogen, methyl, or ethyl and R 8 is hydrogen, methyl, ethyl, methoxy, hydroxy, or chlorine.

Claim 4

The compound of claim 2 wherein R is hydrogen, straight or branched chain alkyl of 1 to 4 carbons, benzyl phenethyl, diphenylmethyl, sodium or potassium; R 2 is lower alkenyl of lower alkinyl wherein said lower alkenyl or lower alkinyl is straight or branched chain alkyl of 1 to 4 carbons; R 3 is hydrogen or straight or branched chain alkyl of 1 to 4 carbons; R 4 is phenyl, benzyl, phenethyl, substituted phenyl, benzyl or phenethyl wherein said substituent is on the phenyl ring and is one or two members selected from the group consisting of chloro, bromo, methyl, ethyl, methoxy, ethoxy and hydroxy, or a substituted or unsubstituted heterocyclic selected from the group consisting of 2-thienyl, 3-thienyl,2-furyl, and 3-furyl, wherein said heterocyclic substituent is attached at an available carbon atom and is chloro, bromo, methyl, or ethyl.

Claim 5

The compound of claim 3 wherein R is hydrogen, sodium or potassium; R 4 is 2-thienyl, 3-thienyl, phenyl or 4-hydroxyphenyl; and R 2 is lower alkenyl of 2 to 4 carbons.

Claim 6

The compound of claim 4 wherein X is ##STR348## and R 7 is hydrogen, methyl, or ethyl.

Claim 7

The compound of claim 5 wherein R is hydrogen and R 7 is methyl.

Claim 8

The compound of claim 4 wherein X is ##STR349## and R 7 is hydrogen, methyl, or ethyl.

Claim 9

The compound of claim 7 wherein R 7 is methyl and R is hydrogen.

Claim 10

The compound of claim 4 wherein X is ##STR350## and R 7 is hydrogen, methyl, or ethyl.

Claim 11

The compound of claim 9 wherein R 7 is methyl and R is hydrogen.

Claim 12

The compound of claim 4 wherein X is ##STR351## and R is hydrogen.

Claim 13

The compound of claim 4 wherein X is ##STR352## and R 7 is hydrogen, methyl, or ethyl.

Claim 14

The compound of claim 12 wherein R 7 is methyl and R is hydrogen.

Claim 15

The compound of claim 4 wherein X is ##STR353## and R 7 is hydrogen, methyl, or ethyl.

Claim 16

The compound of claim 14 wherein R 7 is methyl and R is hydrogen.

Claim 17

The compound of claim 4 wherein X is ##STR354## and R 7 is hydrogen, methyl, or ethyl.

Claim 18

The compound of claim 16 wherein R 7 is hydogen and R is hydrogen.

Claim 19

The compound of claim 4 wherein X is ##STR355## and R 8 is hydrogen, methyl, ethyl, methoxy, hydroxy, or chlorine.

Claim 20

The compound of claim 18 wherein R 8 is hydrogen and R is hydrogen.

Claim 21

The compound of claim 3 wherein X is ##STR356## and R 7 is hydrogen, methyl, or ethyl.

Claim 22

The compound of claim 20 wherein R 7 is methyl.

Claim 23

The compound of claim 21 wherein R is hydrogen, diphenylmethyl, sodium, or potassium; R 4 is 2-thienyl, 3-thienyl, phenyl or 4-hydroxyphenyl; and R 2 is lower alkenyl of 2 to 4 carbons.

Claim 24

The compound of claim 22 wherein R 4 is 2-thienyl.

Claim 25

The compound of claim 23 wherein R 2 is --CH 2 --CH=CH 2 .

Claim 26

The compound of claim 24 wherein R is diphenylmethyl.

Claim 27

The compound of claim 24 wherein R is hydrogen.

Claim 28

The compound of claim 24, 7β-[[D-[[(2-propenylamino) carbonyl]amino]-2-thienylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid.

Claim 29

The compound of claim 24, 7β-[[L-[[(2-propenylamino) carbonyl]amino]-2-thienylacetyl]amino]-3[[(1-methyl-1H-tetrazol-5-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid.

Claim 30

The compound of claim 24 wherein R is sodium.

Claim 31

The compound of claim 29, 7β-[[D-[[(2-propenylamino) carbonyl]amino]-2-thienylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0. [oct-2-ene-2-carboxylic acid, sodium salt.

Claim 32

The compound of claim 29, 7β-[[L-[[(2-propenylamino) carbonyl]amino]-2-thienylacetyl]amino]-3-[[(1methyl-1H-tetrazol-5-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid, sodium salt.

Claim 33

The compound of claim 22 wherein R 2 is --CH=CH 2 .

Claim 34

The compound of claim 32 wherein R is hydrogen.

Claim 35

The compound of claim 32 wherein R is sodium.

Claim 36

The compound of claim 22 wherein R 4 is phenyl.