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US 7,405,201 B2Granted
Antibacterial macrocycles
AssigneeBayer HealthCare LLC
InventorsBerthold Hinzen, Heike Brötz-Oesterhelt, Rainer Endermann, Kerstin Henninger, Holger Paulsen, Siegfried Raddatz, Thomas Lampe, Veronika Hellwig, Andreas Schumacher
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds of the general formula (I), processes for their preparation, pharmaceutical compositions comprising them, and their use in the treatment of diseases in humans or animals.
Claims18
An antibacterial compound of the general formula (I)
- in which
- R1 denotes halogen,
- R2 is hydrogen or halogen,
- R5 denotes hydrogen, C1-C4-alkyl, fluorine or chlorine,
- R6 denotes hydrogen, halogen or alkyl,
- R7 denotes alkyl or (cycloalkyl)alkyl,
- R8a denotes alkyl, alkylene, cycloalkyl or (cycloalkyl)alkyl,
- where R8a optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of hydroxyl, alkoxy, a radical —OR8a-1, carboxyl, alkoxycarbonyl, amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, heterocyclylaminosulfonyl, heteroarylaminosulfonyl, aminocarbonylamino, hydroxycarbonylamino, alkoxycarbonylamino, aminocarbonyloxy, in which R8a-1 is a carbonyl-bonded amino acid radical,
- or R7 and R8a, together with the carbon atom to which R8a is bonded and the nitrogen atom to which R7 is bonded, form a heterocyclyl ring, which optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, azido, amino, alkylamino, dialkylamino, hydroxyl, alkoxy, alkanoyloxy,
- R8a denotes hydrogen or alkyl,
- R9a denotes hydrogen, alkyl, hydroxyalkyl, carboxylalkyl or aminoalkyl,
- R9b denotes hydrogen or alkyl,
- R10a denotes hydrogen, alkyl or fluorine,
- R10b denotes hydrogen or fluorine,
- R11 denotes hydrogen or alkyl,
- R12 denotes alkyl, alkenyl, cycloalkyl, cycloalkenyl, (cycloalkyl)alkyl, (cycloalkenyl)alkyl, (cycloalkyl)alkenyl (cycloalkenyl)alkenyl,
- where R12 optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of halogen, hydroxyl, alkoxy, fluoroalkoxy, aryloxy, alkanoyloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, heteroarylaminosulfonyl, heterocyclylaminosulfonyl, aminocarbonylamino, alkoxycarbonylamino,
- or
- R6 and R12, together with the carbon atom to which they are bonded, form a cycloalkyl, which optionally can be substituted by 1 or 2 substituents, which independently of one another are selected from the group consisting of halogen, hydroxyl, alkoxy,
- R13 denotes hydrogen or alkyl,
- A represents a heterocycle which optionally can be substituted by 1, 2 or 3 sub stituents, which independently of one another are selected from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, amino, alkylamino, dialkylamino, hydroxyl, alkoxy, alkanoyloxy, carboxyl, alkoxycarbonyl, azido, alkoxycarbonylamino,
- represents a single or double bond,
- or a pharmaceutically tolerable salt thereof.
20 more elements
A compound of the general formula (I)
- in which
- R1 denotes halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, amino, alkylamino, dialkylamino or alkylcarbonylamino,
- R2 denotes hydrogen, halogen, alkyl, nitro, amino, alkylamino, dialkylamino, or alkylcarbonylamino,
- R3 denotes hydrogen, halogen, alkyl, nitro, amino, alkylamino, dialkylamino, or alkylcarbonylamino,
- R4 denotes hydrogen, halogen, alkyl, nitro, amino, alkylamino, dialkylamino, or alkylcarbonylamino,
- R5 denotes hydrogen, C1-C4-alkyl, fluorine or chlorine,
- R6 denotes hydrogen, halogen or alkyl,
- R7 and R8a, together with the carbon atom to which R8a is bonded and the nitrogen atom to which R7 is bonded, form a heterocyclyl ring, which optionally can be substituted by 1 or 2 substituents, which independently of one another are selected from the group consisting of halogen, alkyl and amino,
- R8b denotes hydrogen or alkyl,
- R9a denotes hydrogen, alkyl, hydroxyalkyl, carboxylalkyl or aminoalkyl,
- R9b denotes hydrogen or alkyl,
- R10a denotes hydrogen, alkyl or fluorine,
- R10b denotes hydrogen or fluorine,
- R11 denotes hydrogen or alkyl,
- R12 denotes alkyl, alkenyl, cycloalkyl, cycloalkenyl, (cycloalkyl)alkyl, (cycloalkenyl)alkyl, (cycloalkyl)alkenyl (cycloalkenyl)alkenyl,
- where R12 optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of halogen, hydroxyl, alkoxy, fluoroalkoxy, aryloxy, alkanoyloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, heteroarylaminosulfonyl, heterocyclylaminosulfonyl, aminocarbonylamino, alkoxycarbonylamino,
- or
- R6 and R12, together with the carbon atom to which they are bonded, form a cycloalkyl, which optionally can be substituted by 1 or 2 substituents, which independently of one another are selected from the group consisting of halogen, hydroxyl, alkoxy,
- R13 denotes hydrogen or alkyl,
- A represents a heterocycle which optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of halogen, alkyl, tnfluoromethyl, trifluoromethoxy, nitro, amino, alkylamino, dialkylamino, hydroxyl, alkoxy, alkanoyloxy, carboxyl, alkoxycarbonyl, azido, alkoxycarbonylamino,
- repesents a single or double bond,
- or a pharmaceutically tolerable salt thereof.
19 more elements
A compound of the general formula (I)
- in which
- R1 denotes halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, amino, alkylamino, dialkylamino or alkylcarbonylamino,
- R2 denotes hydrogen, halogen, alkyl, nitro, amino, alkylamino, dialkylamino, or alkylcarbonylamino,
- R3 denotes hydrogen, halogen, alkyl, nitro, amino, alkylamino, dialkylamino, or alkylcarbonylamino,
- R4 denotes hydrogen, halogen, alkyl, nitro, amino, alkylamino, dialkylamino, or alkylcarbonylamino,
- R5 denotes hydrogen, C1-C4-alkyl, fluorine or chlorine,
- R6 denotes hydrogen, halogen or alkyl,
- R7 denotes alkyl or (cycloalkyl)alkyl,
- R8a denotes alkyl, alkylene, cycloalkyl or (cycloalkyl)alkyl,
- where R8a optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of hydroxyl, alkoxy, a radical —OR8a-1, carboxyl, alkoxycarbonyl, amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, heterocyclylaminosulfonyl, heteroarylaminosulfonyl, aminocarbonylamino, hydroxycarbonylamino, alkoxycarbonylamino, aminocarbonyloxy, in which R8a-1 is a carbonyl-bonded amino acid radical,
- or R7 and R8a, together with the carbon atom to which R8a is bonded and the nitrogen atom to which R7 is bonded, form a heterocyclyl ring, which optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, azido, amino, alkylamino, dialkylamino, hydroxyl, alkoxy, alkanoyloxy,
- R8b denotes hydrogen or alkyl,
- R9a denotes hydrogen, alkyl, hydroxyalkyl, carboxylalkyl or aminoalkyl,
- R9b denotes hydrogen or alkyl,
- R10a denotes hydrogen, alkyl or fluorine,
- R10b denotes hydrogen or fluorine,
- R11 denotes hydrogen or alkyl,
- R12 denotes C3-C8-alkyl,
- R13 denotes hydrogen or alkyl,
- A represents a heterocycle which optionally can be substituted by 1, 2 or 3 substituents, which independently of one another are selected from the group consisting of halogen, alkyl, trifluoromethyl, trifluoromethoxy, nitro, amino, alkylamino, dialkylamino, hydroxyl, alkoxy, alkanoyloxy, carboxyl, alkoxycarbonyl, azido, alkoxycarbonylamino,
- represents a single or double bond,
- or a pharmaceutically tolerable salt thereof.
19 more elements
Dependencies are inferred from the claim text.