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US 7,598,392 B2Granted
2-amido-4-phenylthiazole derivatives, the preparation and the therapeutic use thereof
AssigneeSanofi-Aventis
InventorsPierre Casellas, Daniel Floutard, Pierre Fraisse, Samir Jegham
Life of this patent
Estimating the term…
Abstract
The disclosure relates to 2-amido-4-phenylthiazole derivatives of general formula (I) below: in which R1, R2, R3, Y, m, n, and p are as defined in the disclosure; as well as to their isomers, salts and solvates, to the pharmaceutical compositions containing them and to the therapeutic use thereof.
Claims17
A compound of formula (I):
- in which:
- R1 represents a hydrogen or halogen atom, a (C1-C4)alkyl, trifluoro(C1-C4)alkyl, hydroxyl, (C1-C4)alkoxy, trifluoro(C1-C4)alkoxy, (C3-C10)cycloalkyl(C1-C4)alkoxy, (C3-C10)cycloalkyloxy, allyloxy or (C1-C4)alkylthio group;
- R2 represents a hydrogen or halogen atom, a hydroxyl, (C1-C4)alkyl, trifluoro(C1-C4)alkyl, perfluoro(C1-C4)alkyl, (C3-C10)cycloalkyl, (C1-C4)alkoxy, (C3-C10)cycloalkyl(C1-C4)alkoxy, (C3-C10)cycloalkyloxy, allyloxy or (C3-C8)cycloalkyl(C1-C4)alkyl group;
- Y represents a hydrogen atom or a halogen;
- R3 represents:
- a phenyl group substituted with one or more:
- fluorine, bromine, iodine,
- ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl,
- (C1-C6)alkoxy,
- —NO2,
- cyano,
- —COR4,
- —SO2R4,
- —CO2R4, in which R4 represents a (C1-C4)alkyl group, or
- —(CH2)qNR5R6, in which R5 and R6 represent, independently of each other, a hydrogen atom or a (C1-C4)alkyl group or R5 and R6 form, together with the nitrogen atom to which they are attached, a 5- or 6-membered cycloalkyl group and q represents 0, 1 or 2;
- or R3 represents a heterocyclic group optionally substituted with one or more:
- halogen,
- (C1-C4)alkyl,
- hydroxyl,
- (C1-C4)alkoxy,
- cyano,
- morpholine,
- trifluoro(C1-C4)alkyl,
- —COR4,
- —SO2R4, in which R4 is as defined hereinabove,
- —(CH2)qNR5R6, in which R5, R6 and q are as defined hereinabove,
- phenyl,
- pyridine, or
- —SCH3;
- the nitrogen atom(s) of the heterocyclic groups which comprise a nitrogen atom(s) may be optionally substituted with a (C1-C4)alkyl group,
- the nitrogen atom(s) of the heterocyclic groups which comprise a nitrogen atom(s) may be optionally in the N-oxide form;
- or R3 represents a heterobicyclic group optionally substituted with one or more halogen, hydroxyl, (C1-C4)alkyl or (C1-C4)alkoxy groups;
- m represents 2, 3 or 4;
- n represents 0, 1 or 2;
- p represents 0, 1, 2 or 3;
- or an addition salt of said compound with a pharmaceutically acceptable acid;
- or a racemic mixture, enantiomer, diastereoisomer or mixture thereof of said compound or said salt.
34 more elements
A compound of formula (I):
- in which:
- R1 represents a hydrogen, chlorine, bromine, iodine, ethyl, propyl, Isopropyl, butyl, isobutyl, tert-butyl, trifluoro(C1-C4)alkyl, hydroxyl, -O-ethyl, -O-propyl, -O-isopropyl. -O-butyl, -O-isobutyl, -O-tert-butyl, trifluoro(C1-C4)alkoxy, (C3-C10)cycloalkyl(C1-C4)alkoxy, (C3-C10)cycloalkyloxy, allyloxy or (C1-C4)alkylthio group;
- R2 represents a hydrogen, chlorine, bromine, iodine, a hydroxyl, (C1-C4)alkyl, trifluoro(C1-C4)alkyl, perfluoro(C1-C4)alkyl, (C3-C 10)cycloalkyl, -O-ethyl, -O-propyl, -O-isopropyl, -O-butyl, -O-isobutyl, -O-tert-butyl, (C3-C10)cycloalkyl(C1-C4)alkoxy, (C3-C10)cycloalkyloxy, allyloxy or (C3-C10)cycloalkyl(C1-C4)alkyl group;
- Y represents a hydrogen atom or a halogen;
- R3 represents:
- a phenyl group substituted with one or more:
- halogen,
- (C1-C6)alkyl,
- (C1-C6)alkoxy,
- —NO2,
- cyano,
- —COR4,
- —SO2R4,
- —CO2R4, in which R4 represents a (C1-C4)alkyl group, or —CH2)qNR5R6, in which R5 and R6 represent, independently of each other, a hydrogen atom or a (C1-C4)alkyl group or R5 and R6 form, together with the nitrogen atom to which they are attached, a 5- or 6-membered cycloalkyl group and q represents 0, 1 or 2;
- or R3 represents a heterocyclic group optionally substituted with one or more:
- halogen,
- (C1-C4)alkyl,
- hydroxyl,
- (C1-C4)alkoxy,
- cyano,
- morpholine,
- trifluoro(C1-C4)alkyl,
- —COR4,
- —SO2R4, in which R4 is as defined hereinabove,
- —(CH2)qNR5R6, in which R5, R6 and q are as defined hereinabove,
- phenyl,
- pyridine, or
- —SCH3;
- the nitrogen atom(s) of the heterocyclic groups which comprise a nitrogen atom(s) may be optionally substituted with a (C1-C4)alkyl group,
- the nitrogen atom(s) of the heterocyclic groups which comprise a nitrogen atom(s) may be optionally in the N-oxide form;
- or R3 represents a heterobicyclic group optionally substituted with one or more halogen, hydroxyl, (C1-C4)alkyl or (C1-C4)alkoxy groups;
- m represents 2, 3 or 4;
- n represents 0, 1 or 2;
- p represents 0, 1, 2 or 3;
- or an addition salt of said compound with a pharmaceutically acceptable acid;
- or a racemic mixture, enantiomer, diastereoisomer or mixture thereof of said compound or said salt.
33 more elements
A compound of formula (I):
- in which:
- R1 represents a hydrogen or halogen atom, a (C1-C4)alkyl, trifluoro(C1-C4)alkyl, hydroxyl, (C1-C4)alkoxy, trifluoro(C1-C4)alkoxy, (C3-C10)cycloalkyl(C1-C4)alkoxy, (C3-C10)cycloalkyloxy, allyloxy or (C1-C4)alkylthio group;
- R2 represents a hydrogen or halogen atom, a hydroxyl, (C1-C4)alkyl, trifluoro(C1-C4)alkyl, perfluoro(C1-C4alkyl, (C3-C 10)cycloalkyl, (C1-C4alkoxy, (C3-C10)cycloalkyl(C1-C4)alkoxy, (C3-C10)cycloalkyloxy, allyloxy or
- (C3-C8)cycloalkyl(C1-C4)alkyl group;
- Y represents a hydrogen atom or a halogen;
- R3 represents:
- a phenyl group substituted with one or more:
- fluorine, bromine, iodine,
- (C1 -C6)alkyl,
- (C1 -C6)alkoxy,
- —NO2,
- cyano,
- —COR4,
- SO2R4,
- —C2R1, in which R4 represents a (C1-C4)alkyl group, or
- —(CH2)qNR5R6, in which R5 and R6 represent, independently of each other, a hydrogen atom or a (C1-C4)alkyl group or R5 and R6 form, together with the nitrogen atom to which they are attached, a 5- or 6-membered cycloalkyl group and q represents 0, 1 or 2;
- or R3 represents a heterocyclic group optionally substituted with one or more:
- halogen,
- (C1-C4)alkyl,
- hydroxyl,
- (C1-C4)alkoxy,
- cyano,
- morpholine,
- trifluoro(C1-C4)alkyl,
- —COR4,
- —SO2R4, in which R4 is as defined hereinabove,
- —(CH2)qNR5R6, in which R5, R6 and q are as defined hereinabove,
- phenyl,
- pyridine, or
- —SCH3;
- the nitrogen atom(s) of the heterocyclic groups which comprise a nitrogen atom(s) may be optionally substituted with a (C1-C4)alkyl group,
- the nitrogen atom(s) of the heterocyclic groups which comprise a nitrogen atom(s) may be optionally in the N-oxide form;
- or R3 represents a heterobicyclic group optionally substituted with one or more halogen, hydroxyl, (C1-C4)alkyl or (C1-C4)alkoxy groups;
- m represents 3 or 4;
- n represents 0, 1 or 2;
- p represents 0, 1,2 or 3;
- or an addition salt of said compound with a pharmaceutically acceptable acid;
- or a racemic mixture, enantiomer, diastereoisomer or mixture thereof of said compound or said salt.
35 more elements
Dependencies are inferred from the claim text.