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US 8,138,336 B2Granted
Pyrrolotriazine derivatives useful for treating cancer through inhibition of aurora kinase
AssigneeBayer HealthCare LLC
InventorsSteven Magnuson, Philip Wickens, Zhonghua Zhang, Ning Qi, Xin Ma
Life of this patent
Estimating the term…
Abstract
This invention relates to novel compounds and processes for their preparation, methods of treating diseases, particularly Cancer, comprising administering said compounds, and methods of making pharmaceutical compositions for the treatment or prevention of disorders, particularly Cancer.
Claims15
A compound having the formula (I):
- or a physiologically acceptable salt or stereoisomer thereof, wherein:
- R1 is -(C1-C4)alkyl, -(C1-C4)alkyl-CF3, -(C3-C6)cycloalkyl, or -(C2-C4)alkyl-NR5R6;
- R2 is hydrogen or -(C1-C4)alkyl;
- R3 is halogen;
- R4 is methyl or ethyl;
- and
- R5 and R6, may be the same or different, and are independently hydrogen, methyl, ethyl, or R5 and R6 may be taken together with the nitrogen to which they are bound to form a pyrrolidine ring.
4 more elements
A compound having the IUPAC name:
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-methylpyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-N-ethyl-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-propylpyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-isobutylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide;
- 4-amino-N-cyclopropyl-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)pyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-N-ethyl-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-methylpyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-N-[2-(dimethylamino)ethyl]-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)pyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-N-tert-butyl-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)pyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-N-tert-butyl-5-(4-{[(6-ethylpyridin-2-yl)carbamoyl]amino}-3-fluorophenyl)pyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(4-{[(6-ethylpyridin-2-yl)carbamoyl]amino}-3-fluorophenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-chloro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-ethylpyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-chloro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-propylpyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-chloro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-cyclopropylpyrrolo[cyclopropylpyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-chloro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-[2-(dimethylamino)ethyl]pyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-chloro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- 4-amino-5-(3-chloro-4-{[(6-ethylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide;
- or a physiologically acceptable salt or stereoisomer thereof.
15 more elements
A salt having the IUPAC name:
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide dimethanesulfonate;
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide hydrochloride;
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide di[(2Z)-but-2-enedioate];
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide (2E)-but-2-enedioate (2:1);
- 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyppyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide hydrobromide;
- 4-amino-5-(4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1 ,2,4]triazine-6-carboxamide oxalate;
- or 4-amino-5-(4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide bisbenzenesulfonate.
4 more elements
Dependencies are inferred from the claim text.