Bicyclic and tricyclic .beta.-lactams

A compound of the formula ##STR24## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butyoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulphur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, lower alkoxy, amino, lower alkanoyloxy, sulfooxy, dimethylamino, or chloroacetylamino, and which is optionally fused to a phenyl ring or 5- or 6-membered heterocycle ring containing 1-3 nitrogen atoms or 1 oxygen atom, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.10 represents hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group, which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.30 represents hydrogen or R.sup.10 and R.sup.30 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• in which R.sup.b represents alkoxy or amino, R.sup.c represents alkyl, phenyl or amino, R.sup.d and R.sup.e each represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, oxygen or sulfur atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above;
• and their pharmaceutically compatible salts.

A compound of the formula ##STR26## wherein R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms, and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, lower alkoxy, amino, lower alkanoyloxy, sulfooxy, dimethylamino, or chloroacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring containing 1-3 nitrogen atoms or 1 oxygen atom, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH--, and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.10 represents hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group, which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.30 represents hydrogen or R.sup.10 and R.sup.30 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents alkoxy or amino, R.sup.c represents alkyl, phenyl or amino, R.sup.d and R.sup.e each represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally be N-substituted or C-substituted by lower alkyl, and Het is as defined above, and their pharmaceutically compatible salts.

A pharmaceutical composition which comprises a therapeutically effective amount of a compound to control or prevent illnesses caused by .beta.-lactamase-forming pathogens having the formula ##STR27## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, lower alkoxy, amino, lower alkanoyloxy, sulfooxy, dimethylamino, or chloroacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring containing 1-3 nitrogen atoms or 1 oxygen atom, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.2 represents the sulpho group --SO.sub.3 H, and in which R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOE.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl, phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above, or the pharmaceutically compatible salts thereof,
• and a pharmaceutically acceptable carrier.

A method of inhibiting .beta.-lactamase in mammals in need of such therapy which comprises administering a therapeutically effective amount of a compound having the formula ##STR28## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, an amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, lower alkoxy, amino, lower alkanoyloxy, sulfooxy, dimethylamino, or chloroacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring containing 1-3 nitrogen atoms or 1 oxygen atom, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.2 represents the sulpho group --SO.sub.3 H, and in which R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl, phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above, or the pharmaceutically compatible salts thereof, and a pharmaceutically acceptable carrier.

A method of inhibiting .beta.-lactamase in mammals in need of such therapy which comprises administering a therapeutically effective amount of a compound having the formula ##STR33## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, an amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, oxo, trifluoroloweralkyl, lower alkoxy, amino, monoloweralkylamino, diloweralkylamino, cycloweralkyl, sulfamoyl, sulfooxy, sulfo, lower alkoxy carbonyl, lower alkoxycarbonylamino, phenyl, 2-methylpropenyl, or 5-amino-1,3,4-thiadiazol-2-ylsulfonylacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.dbd.C(NHOCH.sub.3)--, --CH.sub.2 NH--, --NHCH.sub.2 --, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--CO--NH--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.2 represents the sulpho group --SO.sub.3 H, and in which R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl, phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above, or the pharmaceutically compatible salts thereof,
• and a pharmaceutically acceptable carrier.

A compound of the formula ##STR36## wherein R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms, and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, oxo, trifluoroloweralkyl, lower-alkoxy, amino, monoloweralkylamino, diloweralkylamino, cycloweralkyl, sulfamoyl, sulfooxy, sulfo, lower alkoxy carbonyl, lower alkoxycarbonylamino, phenyl, 2-methylpropenyl, or 5-amino-1,3,4-thiadiazol-2-ylsulfonylacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 .dbd.C(NHCOCH.sub.3)--, --CH.sub.2 NH--, --NHCH.sub.2 --, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--CO--NH--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH--, and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.10 represents hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group, which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.30 represents hydrogen or R.sup.10 and R.sup.30 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents alkoxy or amino, R.sup.c represents alkyl, phenyl or amino, R.sup.d and R.sup.e each represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally be N-substituted or C-substituted by lower alkyl, and Het is as defined above, and their pharmaceutically compatible salts.

A compound of the formula ##STR37## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, or the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, oxo, trifluoroloweralkyl, lower alkoxy, amino, monoloweralkylamino, diloweralkylamino, cycloweralkyl, sulfamoyl, sulfooxy, sulfo, lower alkoxy carbonyl, lower alkoxycarbonylamino, phenyl, 2-methylpropenyl, or 5-amino-1,3,4-thiadiazol-2-ylsulfonylacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.dbd.C(NHCOCH.sub.3)--, --CH.sub.2 NH--, --NHCH.sub.2 --, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--CO--NH--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.2 represents the sulpho group --SO.sub.3 H, and R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• whererin R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl, phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, oxygen or sulfur atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above,
• and their pharmaceutically compatible salts.

A compound of the formula ##STR38## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butyoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulphur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, oxo, trifluoroloweralkyl, lower alkoxy, amino, monoloweralkylamino, diloweralkylamino, cycloweralkyl, sulfamoyl, sulfooxy, sulfo, lower alkoxy carbonyl, lower alkoxycarbonylamino, phenyl, 2-methylpropenyl, or 5-amino-1,3,4-thiadiazol-2-ylsulfonylacetylamino, and which is optionally fused to a phenyl ring or 5- or 6-membered heterocycle ring, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.dbd.C(NHOCH.sub.3)--, --CH.sub.2 NH--, --NHCH.sub.2 --, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--CONH--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.10 represents hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group, which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.30 represents hydrogen or R.sup.10 and R.sup.30 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• in which R.sup.b represents alkoxy or amino, R.sup.c represents alkyl, phenyl or amino, R.sup.d and R.sup.e each represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, oxygen or sulfur atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above;
• and their pharmaceutically compatible salts.

A pharmaceutical composition which comprises a therapeutically effective amount of a compound having the formula ##STR39## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the carboxylic acyl residue of an .alpha.- or .beta.-amino acid, the amino group of said .alpha.- or .beta.-amino acid being optionally substituted by lower alkyl, phenyl, lower alkanoyl, benzoyl, benzyloxycarbonyl, t-butoxycarbonyl, (4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl or (4-hydroxy-6-methyl-3-pyridyl)carbonyl, or a residue of the formula

• Q--X--Y-- (a)
• wherein Q signifies a 3- to 6-membered ring which optionally contains 1-4 nitrogen atoms and/or 1-2 sulfur or oxygen atoms and which is optionally substituted by hydroxy, halogen, lower alkyl, oxo, trifluoroloweralkyl, lower alkoxy, amino, monoloweralkylamino, diloweralkylamino, cycloweralkyl, sulfamoyl, sulfooxy, sulfo, lower alkoxy carbonyl, lower alkoxycarbonylamino, phenyl, 2-methylpropenyl, or 5-amino-1,3,4-thiadiazol-2-ylsulfonylacetylamino, and which is optionally fused to a phenyl ring or a 5- or 6-membered heterocycle ring, X signifies a direct bond or represents one of --O--, --S--, --NH--, --NH--NH--, --CO--NH--NH--, --CH.sub.2 --, --CO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.dbd.C(NHCOCH.sub.3)--, --CH.sub.2 NH--, --NHCH.sub.2 --, --S--CH.sub.2 --, --SO.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CH.sub.2 --O--NH--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--CO--NH--CH.sub.2 CH.sub.2 --, --CHOH--, --CH(COOH)--, --CH(OSO.sub.3 H)--, --CH(OCONH.sub.2)--, and --CH CH(CH.sub.3).sub.2 !--, and Y represents one of the groups --CO--, --CS--, --CONH-- and --SO.sub.2 --, except that when Y is --SO.sub.2 --, X represents one of --O--, --NH--, --NH--NH--, --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 NH--, O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --NH--, --CHOH--, and --CH CH(CH.sub.3).sub.2 !--;
• R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino, and R.sup.2 represents the sulpho group --SO.sub.3 H, and in which R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above, or the pharmaceutically compatible salts thereof,
• and a pharmaceutically acceptable carrier.

A compound of the formula ##STR40## wherein R.sup.1 is hydrogen, halogen, carbamoyloxy, lower alkanoyloxy, or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group which contains 1-4 nitrogen atoms and/or 1 sulfur or oxygen atom and which is optionally substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyloxy, halogen, amino, dimethylamino, or chloroacetylamino;

• R.sup.2 is the sulpho group --SO.sub.3 H;
• and R.sup.3 represents hydrogen or R.sup.1 and R.sup.3 together represent a group of the formula
• .dbd.CH--R.sup.a (c)
• wherein R.sup.a signifies one of the groups
• --COR.sup.b (c.sup.1)
• --CH.sub.2 --OCOR.sup.c (c.sup.2)
• --CH.sub.2 --NR.sup.d R.sup.e (c.sup.3)
• --CH.sub.2 --S--Het (c.sup.4)
• where R.sup.b represents lower alkoxy or amino, R.sup.c represents lower alkyl, phenyl or amino, R.sup.d and R.sup.e each independently represent hydrogen or lower alkyl or R.sup.d and R.sup.e together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle ring which optionally contains an additional nitrogen, sulfur or oxygen atom, said N-heterocycle ring optionally N-substituted or C-substituted by lower alkyl, and Het is as defined above,
• and their pharmaceutically compatible salts.