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US 6,602,884 B2Granted
Quinolylpropylpiperidine derivatives, their preparation, and compositions containing them
AssigneeAventis Pharma S.A.
InventorsEric Bacqué, Serge Mignani, Jean-Luc Malleron, Michel Tabart, Michel Evers, Fabrice Viviani, Youssef El Ahmad, Stéphane Mutti, Christophe Daubié
Life of this patent
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Abstract
Quinolylpropylpiperidine derivatives of general formula (I) are described, and are useful as antimicrobial agents. Their preparation is also described.
Claims20
A quinolylpropylpiperidine derivative compound of formula (I)
- wherein:
- R1 represents a hydrogen atom, a halogen atom, or a hydroxyl, amino, alkylamino, dialkylamino, hydroxyamino, alkyloxyamino, or alkylalkyloxyamino radical;
- R2 represents a carboxyl, carboxymethyl, or hydroxymethyl radical;
- R3 represents an alkyl radical having 1 to 6 carbon atoms, which is substituted with:
- a phenylthio radical, which is optionally substituted with 1 to 4 substituents chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoro-methoxy, carboxyl, alkyloxycarbonyl, cyano, and amino,
- a cycloalkylthio radical in which the cyclic portion contains 3 to 7 members, or
- a 5- to 6-membered aromatic heterocyclylthio radical with 1 to 4 heteroatoms chosen from nitrogen, oxygen, and sulfur, and wherein HENDERSON the 5- to 6-membered aromatic heterocyclylthio radical is optionally substituted with at least one radical chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoro-methoxy, oxo, carboxyl, alkyloxycarbonyl, cyano, and amino;
- or
- R3 represents a propargyl radical substituted with:
- a phenyl radical, which is optionally substituted with 1 to 4 substituents chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, carboxyl, alkyloxycarbonyl, cyano, and amino,
- a 3- to 7-membered cycloalkyl radical, or
- a 5- to 6-membered aromatic heterocyclyl radical with 1 to 4 heteroatoms chosen from nitrogen, oxygen, and sulfur, and wherein the 5- to 6-membered aromatic heterocyclyl radical is optionally substituted with at least one radical chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, oxo, carboxyl, alkyloxycarbonyl, cyano, and amino;
- and
- R4 represents an alkyl radical containing 1 to 6 carbon atoms, an alkenyl-CH2—, alkynyl-CH2—, cycloalkyl, or cycloalkylalkyl radical, wherein the alkenyl and alkynyl portions contain 2 to 6 carbon atoms and the cycloalkyl portions contain 3 to 8 carbon atoms,
- wherein the alkyl radicals and portions are in the form of a straight or branched chain and contain, unless otherwise stated, 1 to 4 carbon atoms,
- or a diastereoisomeric form, a cis form, or a trans form of a compound of formula (I) or a mixture thereof, or a salt thereof.
13 more elements
A quinolylpropylpiperidine derivative of formula (IV):
- wherein
- R′2 represents a protected carboxyl or carboxymethyl radical;
- R3 represents an alkyl radical having 1 to 6 carbon atoms, which is substituted with:
- a phenylthio radical, which is optionally substituted with 1 to 4 substituents chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoro-methoxy, carboxyl, alkyloxycarbonyl, cyano, and amino,
- a cycloalkylthio radical in which the cyclic portion contains 3 to 7 members, or
- a 5- to 6-membered aromatic heterocyclylthio radical with 1 to 4 heteroatoms chosen from nitrogen, oxygen, and sulfur, and wherein the 5- to 6-membered aromatic heterocyclylthio radical is optionally substituted with at least one radical chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoro-methoxy, oxo, carboxyl, alkyloxycarbonyl, cyano, and amino;
- or
- R3 represents a propargyl radical substituted with:
- a phenyl radical, which is optionally substituted with 1 to 4 substituents chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, carboxyl, alkyloxycarbonyl, cyano, and amino,
- a 3- to 7-membered cycloalkyl radical,
- a 5- to 6-membered aromatic heterocyclyl radical with 1 to 4 heteroatoms chosen from nitrogen, oxygen, and sulfur, and wherein the 5- to 6-membered aromatic heterocyclyl radical is optionally substituted with at least one radical chosen from halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, oxo, carboxyl, alkyloxycarbonyl, cyano, and amino;
- R4 represents an alkyl radical containing 1 to 6 carbon atoms, an alkenyl-CH2—, alkynyl-CH2—, cycloalkyl, or cycloalkylalkyl radical, wherein the alkenyl and alkynyl portions contain 2 to 6 carbon atoms and the cycloalkyl portion contains 3 to 8 carbon atoms, and
- R5 represents a hydrogen atom or an alkyl radical;
- wherein the alkyl radicals and portions are in the form of a straight or branched chain and contain, unless otherwise stated, 1 to 4 carbon atoms.
11 more elements
Dependencies are inferred from the claim text.