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US 9,845,323 B2Granted
2-(1,3,4-oxadiazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1 ]octane derivatives and their use as antibacterial agents
AssigneeWockhardt Limited
InventorsSanjay Raikar, Sanjay Kisan Dabhade, Laxmikant Pavase, Sachin Bhagwat, Ravindra Dattatraya Yeole, Mahesh Vithalbhai Patel
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Abstract
Compounds of Formula (I), their preparation, and use in preventing or treating a bacterial infection are disclosed.
Claims19
A compound of Formula (I):
- or a stereoisomer or a pharmaceutically acceptable salt thereof;
- wherein:
- R1 is:
- (a) C1-C6 alkyl substituted with aryl;
- (b) aryl optionally substituted with one or more substituents independently selected from C1-C6 alkyl, halogen, CN, OR3, NR3R4, or CONR3R4;
- R2 is:
- (a) SO3M;
- R3 and R4 are each independently:
- (a) hydrogen, or
- (b) C1-C6 alkyl optionally substituted with one or more substitutents independently selected from halogen, CN, OH, O(C1-C6 alkyl), NH(C1-C6 alkyl), N(C1-C6 alkyl)2, CONH(C1-C6 alkyl), CON(C1-C6 alkyl)2 or aryl;
- wherein M is hydrogen or a cation.
8 more elements
A compound selected from:
- (2S,5R)-sulfuric acid mono-[2-(5-benzyl-[1,3,4]-oxadiazol-2-yl)-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl] ester;
- (2S,5R)-sulfuric acid mono-[2-(5-phenyl-ethyl-[1,3,4]-oxadiazol-2-yl)-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl] ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(3-phenyl-propyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- (2S,5R)-sulfuric acid mono-[2-(5-benzhydryl-[1,3,4]-oxadiazol-2-yl)-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl] ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(2,2-diphenyl-ethyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(4-amino-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(4-dimethylamino-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(4-hydroxy-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- (2S,5R)-sulfuric acid mono-{2-[5-(4-methoxy-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- or a stereoisomer or a pharmaceutically acceptable salt thereof.
8 more elements
A compound is selected from:
- sodium salt of (2S,5R)-sulfuric acid mono-[2-(5-benzyl-[1,3,4]-oxadiazol-2-yl)-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl] ester;
- sodium salt of (2S,5R)-sulfuric acid mono-[2-(5-phenyl-ethyl-[1,3,4]-oxadiazol-2-yl)-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl] ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(3-phenyl-propyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- sodium salt of (2S,5R)-sulfuric acid mono-[2-(5-benzhydryl-[1,3,4]-oxadiazol-2-yl)-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl] ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(2,2-diphenyl-ethyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(4-amino-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(4-dimethylamino-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(4-hydroxy-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- sodium salt of (2S,5R)-sulfuric acid mono-{2-[5-(4-methoxy-benzyl)-[1,3,4]-oxadiazol-2-yl]-7-oxo-1,6-diaza-bicyclo[3.2.1] oct-6-yl} ester;
- or a stereoisomer thereof.
8 more elements
Dependencies are inferred from the claim text.