3-Heterocyclylthiomethyl cephalosporins

Claim 2

Acyl derivatives of the general formula in which A signifies a group of the general formulae -NHCO-, -NHCONHCO-, -NHCOCH=CH-, wherein R⁶ represents hydrogen or lower alkyl; R¹ and R² in each case signify hydrogen or a protecting group, X signifies hydrogen, halogen, lower alkoxy, nitro or an additional group -OR², n signifies the number 1 or 2, R⁴ and R⁵ both signify hydrogen or together signify an additional bond and Z signifies a direct bond or carbonyl (where R⁴ and R⁵ both represent hydrogen) or a group of the formula -O-B- (where R⁴ and R⁵ together represent an additional bond) in which B signifies straight-chain, branched or cyclic lower alkylene; and wherein further R³ signifies a substituted bicyclic group of the general formulae in which R⁷ and R⁸ each individually represent hydrogen, lower alkyl or trifluoromethyl or (in formulae (a), (b), (e) and (f)) together represent alkylene with 3 or 4 carbon atoms and Rʹ, Rʺ and R‴ each individually represent hydrogen, lower alkyl or lower cycloalkyl; whereby compounds of formula I in which R⁴ and R⁵ together represent an additional bond are present in the syn-isomeric form or as a mixture with the anti-isomeric form in which the syn-isomeric form predominates, as well as readily hydrolyzable esters and salts of these compounds and hydrates of the compounds of formula I or of their esters and salts.

Claim 3

Acyl derivatives according to claim 1 of the general formula in which R³ and B have the significance given in claim 1, and X¹ represents hydrogen or chlorine, as well as readily hydrolyzable esters and salts of these compounds and hydrates of the compounds of formula Ia or of their esters and salts.

Claim 4

Compounds according to claim 1 or 2, wherein B represents the group -C(CH₃)₂- or -CH₂-.

Claim 5

Compounds according to any one of claims 1-3, wherein the groups -(OR²)₂ and -(OH)₂, respectively, are present in the 3,4- or 2,3-position.

Claim 6

Compounds according to any one of claims 1-4, wherein R³ represents one of the groups wherein Rʹ, Rʺ, R⁷ and R⁸ have the significance given in claim 1.

Claim 7

Compounds according to any one of claims 1-4, wherein R³ represents one of the groups wherein Rʹ, Rʺ, R⁷ and R⁸ have the significance given in claim 1.

Claim 8

Compounds according to any one of claims 1-4, wherein R³ signifies a carbamoyl-substituted bicyclic group of the general formulae wherein R⁷⁰ and R⁸⁰ each individually represent hydrogen, methyl or trifluoromethyl or together represent alkylene with 3 or 4 carbon atoms.

Claim 9

Compounds according to any one of claims 1-4, wherein R³ signifies a substituted bicyclic group of the general formulae wherein R⁷⁰ and R⁸⁰ each individually represent hydrogen, methyl or trifluoromethyl or together represent alkylene with 3 or 4 carbon atoms and R‴ signifies hydrogen or methyl.

Claim 10

Compounds according to any one of claims 1-4, wherein R³ represents one of the groups wherein R⁷¹ represents methyl or trifluoromethyl and R⁸¹ represents hydrogen or R⁷¹ and R⁸¹ together represent tetramethylene and Rʺʺ signifies hydrogen or methyl.

Claim 11

Compounds according to claim 7, wherein R³ represents group (a⁴) which is linked via position 5:

Claim 12

Compounds according to claim 7, wherein R³ represents group (a⁴) which is linked via position 7:

Claim 13

Compounds according to any one of claims 7, 10 and 11, wherein R³ represents group (a⁴) in which the carbamoyl group is present in position 3:

Claim 14

Compounds according to claim 11 or 12, wherein R³ represents the group

Claim 15

Compounds according to claim 7, wherein R³ represents group (b⁴) which is linked via position 5:

Claim 16

Compounds according to claim 7, wherein R³ represents group (b⁴) which is linked via position 7:

Claim 17

Compounds according to claim 14 or 15, wherein R³ represents the group

Claim 18

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazoly])-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo[1,5-a]­pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 19

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazoly])-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo[1,5-a]­pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 20

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]­pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 21

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]­pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 22

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­ acetamido]-3-[[(2-carbamoyl-6.7-dihydro-5H-cyclopenta[d]-s­-triazolo[1,5-a]pyrimidin-8-yl)thio]methyl]-8-oxo-5­-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 23

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­ acetamido]-3-[[(2-carbamoyl-6.7-dihydro-5H-cyclopenta[d]-s­-triazolo[1,5-a]pyrimidin-8-yl)thio]methyl]-8-oxo-5­-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 24

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carbamoyl-7-methyl-s-triazolo[1,5-a]­pyrimidin-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 25

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carbamoyl-7-methyl-s-triazolo[1,5-a]­pyrimidin-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 26

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido-3-[[[3-carbamoyl-7-(trifluoromethyl)pyrazolo­[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 27

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido-3-[[[3-carbamoyl-7-(trifluoromethyl)pyrazolo­[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 28

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-carbamoyl-5-(trifluoromethyl)pyrazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabi­cyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 29

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-carbamoyl-5-(trifluoromethyl)pyrazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabi­cyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 30

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(2,3-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo[1,5-a]­pyrimidin-7-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 31

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(2,3-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo[1,5-a]­pyrimidin-7-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 32

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carboxy-7-methyl-s-triazolo[1,5-a]­pyrimidin-5-yl)thio]-methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazoalyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­ acetamido]-3-[[(2-methoxycarbonyl-7-methyl-s-triazolo­[1,5-a]pyrimidin-5-yl)thio]-methyl]-8-oxo-5-thia-1-aza­bicyclo-[4.2.0]oct-2-ene-2-carboxylic acid. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-(cyclopropylcarbamoyl)-7-methyl-s-tri­azolo[1,5-a]-pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-(methoxycarbonyl)-7-methylpyrazolo[1,5-a]­pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[[[(Z)-2-(2-amino-4-thiazolyl)-2-[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-carboxy-7-(trifluoromethyl)pyrazolo­[1,5-a]-pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and salts of any of these compounds.

Claim 33

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(2-carboxy-7-methyl-s-triazolo[1,5-a]­pyrimidin-5-yl)thio]-methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazoalyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­ acetamido]-3-[[(2-methoxycarbonyl-7-methyl-s-triazolo­[1,5-a]pyrimidin-5-yl)thio]-methyl]-8-oxo-5-thia-1-aza­bicyclo-[4.2.0]oct-2-ene-2-carboxylic acid. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-(cyclopropylcarbamoyl)-7-methyl-s-tri­azolo[1,5-a]-pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-(methoxycarbonyl)-7-methylpyrazolo[1,5-a]­pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[[[(Z)-2-(2-amino-4-thiazolyl)-2-[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-carboxy-7-(trifluoromethyl)pyrazolo­[1,5-a]-pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and salts of any of these compounds.

Claim 34

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[5-methyl-2-(methylcarbamoyl)-s-triazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 35

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[5-methyl-2-(methylcarbamoyl)-s-triazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 36

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-(dimethylcarbamoyl)-5-methyl-s-tri­azolo[1,5-a]-pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and its salts.

Claim 37

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-(dimethylcarbamoyl)-5-methyl-s-tri­azolo[1,5-a]-pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and its salts.

Claim 38

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carbamoyl-5-(trifluoromethyl)-s-triazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 39

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carbamoyl-5-(trifluoromethyl)-s-triazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 40

(6R,7R)-7-[(Z)-2-[2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carbamoyl-7-(trifluoromethyl)-s-triazolo­[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 41

(6R,7R)-7-[(Z)-2-[2-Amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carbamoyl-7-(trifluoromethyl)-s-triazolo­[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 42

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-(3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carboxy-7,8-dihydro-6H-cyclopenta[e]­[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5­-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino­[-acetamido]-3-[[[2-carbamoyl-7,8-dihydro-6H-cyclopenta[e]­[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5­-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(3­-[3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carboxy-7-(trifluormethyl)-s-triazolo­[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-6,7-dihydro-5H-cyclopenta[d]­pyrazolo[1,5-a]pyrimidin-8-yl)thio]methyl]-8-oxo-5-thia-1­-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-6,7-dihydro-5H-cyclopenta[d] pyrazolo[1,5-a]pyrimidin-8-yl)thio]methyl]-8-oxo-5-thia-1­-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-5-methyl-pyrazolo[1,5-a]­pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-(dimethylcarbamoyl)-5-methyl-pyrazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-(dimethylcarbamoyl)-5-methyl-pyrazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and salts of any of these compounds.

Claim 43

(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-(3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carboxy-7,8-dihydro-6H-cyclopenta[e]­[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5­-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino­[-acetamido]-3-[[[2-carbamoyl-7,8-dihydro-6H-cyclopenta[e]­[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5­-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(3­-[3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[2-carboxy-7-(trifluormethyl)-s-triazolo­[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-6,7-dihydro-5H-cyclopenta[d]­pyrazolo[1,5-a]pyrimidin-8-yl)thio]methyl]-8-oxo-5-thia-1­-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-6,7-dihydro-5H-cyclopenta[d] pyrazolo[1,5-a]pyrimidin-8-yl)thio]methyl]-8-oxo-5-thia-1­-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[(3-carbamoyl-5-methyl-pyrazolo[1,5-a]­pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo­[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-(dimethylcarbamoyl)-5-methyl-pyrazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid, (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]­acetamido]-3-[[[3-(dimethylcarbamoyl)-5-methyl-pyrazolo­[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-aza­bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and salts of any of these compounds.

Claim 44

(6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­(3-chloro-4,5-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]­imino]acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo­[1,5-a]pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabi­cyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 45

(6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3­(3-chloro-4,5-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]­imino]acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo­[1,5-a]pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabi­cyclo[4.2.0]oct-2-ene-2-carboxylic acid and its salts.

Claim 46

Compounds according to any one of claims 1-30 as pharmaceutically active substances.

Claim 47

Compounds according to any one of claims 1-30 as pharmaceutically active substances for the treatment and prophylaxis of infectious diseases.

Claim 48

A process for the manufacture of the compounds in accordance with any one of claims 1-30, which process comprises (a) reacting a compound of the general formula in which R³ has the significance given in claim 1 and M represents hydrogen or an ester protecting group, with a carboxylic acid of the general formula in which R¹, R², R⁴, R⁵, X, Z, A and n have the significance given in claim 1, or one of its reactive derivatives and, if desired, cleaving off any protecting groups, or (b) reacting a compound of the general formula in which R¹, R², R⁴, R⁵, X, Z, A and n have the significance given in claim 1, M has the signi­ficance given above and Y represents a leaving group, with a compound of the general formula HSR³      VI in which R³ has the significance given in claim 1, and if desired. cleaving off any protecting groups, or (c) reacting a compound of the general formula in which R¹, R³, R⁴, R⁵ and Z have the signi­ficance given in claim 1 and M has the above signi­ficance, with a compound of the general formulae in which R², R⁶, X and n have the significance given in claim 1, or a reactive derivative of one of the carboxylic acids VIIIa and VIIIc and, if desired, cleaving off any protecting groups, or (d) for the manufacture of compounds of formula I in which R⁴ and R⁵ together represent an additional bond, reacting a compound of the general formula wherein R¹ and R³ have the significance given in claim 1, with a salt of a compound of the general formula in which R², A, B, X and n have the significance given in claim 1, or (e) for the manufacture of a readily hydrolyzable ester of a compound of formula I, subjecting a carboxylic acid of formula I to an appropriate esterification, or (f) for the manufacture of salts and hydrates of a compound of formula I or of hydrates of these salts, con­verting a compound of formula I into a salt or hydrate or into a hydrate of this salt.

Claim 49

Pharmaceutical preparations, which contain a compound in accordance with any one of claims 1-30.

Claim 50

Pharmaceutical preparations for the treatment and prophylaxis of infectious diseases, said preparations containing a compound in accordance with any one of claims 1-30.

Claim 51

The use of compounds in accordance with any one of claims 1-30 in the treatment or prophylaxis of ill­nesses.

Claim 52

The use of compounds in accordance with any one of claims 1-30 in the treatment or prophylaxis of infectious diseases.

Claim 53

The use of compounds in accordance with any one of claims 1-30 in the manufacture of medicaments for the treatment or prophylaxis of infectious diseases.