Indazolecarboxamide derivatives, preparation and use thereof as CDK1, CDK2 and CDK4 inhibitors
AssigneeSanofi-Aventis
InventorsHugues D'Orchymont, Luc Van Hijfte, Andre Zimmermann
Life of this patent
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Abstract
Compound corresponding to general formula (I): in which, R1 represents a hydrogen or halogen atom, an NH2, NHR2, NHCOR2, NO2, CN, CH2NH2 and CH2NHR2; or alternatively R1 represents an optionally substituted phenyl or an optionally substituted heteroaromatic group; Ar represents an optionally substituted phenyl group or an optionally substituted heteroaromatic group; n represents 0, 1, 2 or 3; in the form of a base, of an addition salt with an acid, of a hydrate or of a solvate. Application in therapy.
Claims13
A compound corresponding to general formula (I):
- in which,
- R1 represents
- a heteroaromatic group optionally substituted with one or two substituents selected from a halogen atom, a hydroxyl, a heteroaromatic group, C1-6 alkyl, NH2, NHR2, NHCOR2, COOR2, CONH2, CONHR2 and CH2XR2 where X represents an atom selected from O, NH and S;
- and
- Ar represents
- a heteroaromatic group, optionally substituted with one or two substituents selected from a halogen atom, C1-6 alkyl, C1-6 thioalkyl, C1-6 alkoxy, CH2OH, phenoxy, morpholinyl, —CH2-morpholinyl, NH2, NHR2, NR2R3, NHSO2R2, CN, SO2R2, SO2NH2, SO2NHR2, COOH, COOR2, CONH2, CONHNH2, CONHR2, CH2NHR2 and CH2NR2R3;
- and wherein
- R2 and R3 represent, independently of each other, a C1-6 alkyl optionally substituted with a CONH2 group, with a phenyl or with a heteroaromatic group;
- or R2 and R3 represent, independently of each other, a phenyl or a heteroaromatic group;
- and
- n represents 0, 1, 2 or 3;
- or a salt thereof, or a hydrate or a solvate thereof.
A compound of general formula (V)
- in which
- R1 represents
- a heteroaromatic group optionally substituted with one or two substituents selected from a halogen atom, a hydroxyl, a heteroaromatic group, C1-6 alkyl, NH2, NHR2, NHCOR2, COOR2, CONH2, CONHR2 and CH2XR2 where X represents an atom selected from O, NH and S;
- and
- PG represents a protecting group of the trimethylsilylethoxymethyl (SEM) or mesitylenesulphonyl (Mts) type.
A compound of general formula (VII)
- in which
- R1 represents
- a heteroaromatic group optionally substituted with one or two substituents selected from a halogen atom, a hydroxyl, a heteroaromatic group, C1-6 alkyl, NH2, NHR2, NHCOR2, COOR2, CONH2, CONHR2 and CH2XR2 where X represents an atom selected from O, NH and S;
- Ar represents
- a heteroaromatic group, optionally substituted with one or two substituents selected from a halogen atom, C1-6 alkyl, C1-6 thioalkyl, C1-6 alkoxy, CH2OH, phenoxy, morpholinyl, NH2, NHR2, NR2R3, NHSO2R2, CN, SO2R2, SO2NH2, SO2NHR2, COOH, COOR2, CONH2, CONHNH2, CONHR2 and CH2NHR2;
- and wherein
- R2 and R3 represent, independently of each other, a C1-6 alkyl optionally substituted with a CONH2, a phenyl or a heteroaromatic group;
- or R2 and R3 represent, independently of each other, a phenyl or a heteroaromatic group;
- n represents 0, 1, 2 or 3;
- and
- PG represents a protecting group of the trimethylsilylethoxymethyl (SEM) or mesitylenesuiphonyl (Mts) type.
A compound of general formula (X)
- in which
- Ar represents
- a heteroaromatic group, optionally substituted with one or two substituents selected from a halogen atom, C1-6 alkyl, C1-6 thioalkyl, C1-6 alkoxy, CH2OH, phenoxy, morpholinyl, NH2, NHR2, NR2R3, NHSO2R2, CN, SO2R2, SO2NH2, SO2NHR2, COOH, COOR2, CONH2, CONHNH2, CONHR2 and CH2NHR2;
- and wherein
- R2 and R3 represent, independently of each other, a C1-6 alkyl optionally substituted with a CONH2, a phenyl or a heteroaromatic group;
- or R2 and R3 represent, independently of each other, a phenyl or a heteroaromatic group;
- n represents 0, 1, 2 or 3;
- SEM represents a protecting group of trimethylsilylethoxymethyl type;
- and
- X represents a bromine or iodine atom.
Dependencies are inferred from the claim text.