Heterocyclic compounds and uses thereof
AssigneeInfinity Pharmaceuticals, Inc.
InventorsAlfredo C. CASTRO, Catherine A. EVANS, Martin R. TREMBLAY
Life of this patent
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Abstract
Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
Claims22
A compound of Compound 1 or Compound 96:
- or an enantiomer, a mixture of enantiomers, a pharmaceutically acceptable form thereof.
A compound, wherein the compound is selected from a compound in Table 1, Table 2, Table 2, Table 3, Table 4, Table 5, or Table 6.
A process of preparing a (S)-3-(1-((9H-purin-6-yl)amino)propyl)-8-fluoro-2-phenylisoquinolin-1(2H)-one (Compound 1s) comprising:
- deprotecting 8-fluoro-2-phenyl-3-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)isoquinolin-1(2H)-one to form (S)-3-(1-((9H-purin-6-yl)amino)propyl)-8-fluoro-2-phenylisoquinolin-1 (2H)-one.
A process of preparing a (S)-3-(1-((9H-purin-6-yl)amino)propyl)-8-fluoro-2-phenylisoquinolin-1(2H)-one (Compound 1s) comprising:
- contacting 2-fluoro-6-methyl-N-phenylbenzamide with (S)-tert-butyl (1-(methoxy(methyl)amino)-1-oxobutan-2-yl)carbamate to form (S)-tert-butyl (1-(3-fluoro-2-(phenylcarbamoyl)phenyl)-2-oxopentan-3-yl)carbamate;
- contacting (S)-tert-butyl (1-(3-fluoro-2-(phenylcarbamoyl)phenyl)-2-oxopentan-3-yl)carbamate with an acid to form (S)-3-(1-aminopropyl)-8-fluoro-2-phenylisoquinolin-1(2H)-one;
- contacting (S)-3-(1-aminopropyl)-8-fluoro-2-phenylisoquinolin-1(2H)-one with 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine to form 8-fluoro-2-phenyl-3-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)isoquinolin-1 (2H)-one;
- and
- deprotecting 8-fluoro-2-phenyl-3-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)isoquinolin-1(2H)-one to form (S)-3-(1-((9H-purin-6-yl)amino)propyl)-8-fluoro-2-phenylisoquinolin-1 (2H)-one.
A process of preparing 8-fluoro-2-phenyl-3-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)isoquinolin-1 (2H)-one comprising contacting (S)-3-(1-aminopropyl)-8-fluoro-2-phenylisoquinolin-1(2H)-one with 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine to form 8-fluoro-2-phenyl-3-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)isoquinolin-1(2H)-one.
Dependencies are inferred from the claim text.