Alkylthiazol carbamate derivatives, preparation thereof and therapeutic use thereof
AssigneeSanofi
InventorsAhmed Abouabdellah, Jochen Görlitzer, Peter Hamley, Antoine Ravet
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Abstract
The invention relates to the novel products of formula (I): in which: Ra represents H, Hal, aryl or heteroaryl, which is optionally substituted; Rb represents H, Rc, —COORc-CO—Rc or —CO—NRcRd; where Rc represents alkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl, all optionally substituted; Rd represents H, alk or cycloalkyl; these products being in all the isomer forms and the salts, as medicaments, in particular as MET inhibitors.
Claims11
Compound of the formula (I)
- in which
- R2 represents a hydrogen or fluorine atom, a hydroxyl, cyano, trifluoromethyl, C1-6 alkyl or C1-6 alkoxy group or a group NR8R9;
- n represents an integer 2 and m represents an integer 2;
- A represents a covalent bond or a C1-8 alkylene group;
- R1 represents a group R5 which is optionally substituted by one or more groups R6 and/or R7;
- R5 represents a pyridinyl group;
- R6 represents a halogen atom, a cyano, —CH2CN, nitro, hydroxyl, C1-6 alkyl, C1-6 alkoxy, C1-6 thioalkyl, C1-6 haloalkyl, C1-6 haloalkoxy, C1-6 halothioalkyl, C3-7 cycloalkyl, C3-7 cycloalkyl-C1-3 alkylene or C3-7 cycloalkyl-C1-3 alkylene-O— group, or a group NR8R9, NR8COR9, NR8CO2R9, NR8SO2R9, NR8SO2NR8R9, COR8, CONR8R9, SO2R8, SO2NR8R9 or —O—(C1-3-alkylene)-O—;
- R7 represents a group selected from a thienyl, isoxazolyl, pyrazolyl, phenyl, pyridinyl, pyrimidinyl, naphthalenyl, quinolinyl or isoquinolinyl, the group or groups R7 being able to be substituted by one or more groups R6 which are identical or different from one another;
- R3 represents a hydrogen or fluorine atom, a C1-6 alkyl group or a trifluoromethyl group;
- R4 represents a thiazole which is optionally substituted by one or more substituents selected from a C1-6 alkyl and CONR8R9;
- R8 and R9 represent independently of one another a hydrogen atom or a C1-6 alkyl group, or form, with the atom or atoms bearing them,
- in the case of NR8R9, a ring selected from azetidine, pyrrolidine, piperidine, morpholine, thiomorpholine, azepine, oxazepine or piperazine ring, this ring being optionally substituted by a C1-6 alkyl or benzyl group;
- in the case of NR8COR9, a lactam ring;
- in the case of NR8CO2R9, an oxazolidinone, oxazinone or oxazepinone ring;
- in the case of NR8SO2R9, a sultam ring;
- in the case of NR8SO2NR8R9, a thiazolidine dioxide or thiadiazinane dioxide ring;
- in the form of the base or an addition salt with an acid.
A compound selected from the group consisting of thiazol-2-ylmethyl{1-[5-(4-fluorophenyl)pyridin-2-yl]pyrrolidin-3-yl)}methylcarbamate and thiazol-4-ylmethyl {1-[5-(4-fluorophenyl)pyridin-2-yl]pyrrolidin-3-yl)}methylcarbamate;
- in the form of the base or an addition salt with an acid.
Dependencies are inferred from the claim text.