Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use
AssigneeGilead Calistoga LLC
InventorsJerry B. Evarts, Roger G. Ulrich
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Abstract
The invention provides compounds, compositions and methods to treat certain inflammatory conditions and/or oncology by administering a compound that inhibits PI3K isoforms, particularly the delta isoform. It further provides specific stereoisomers of a compound useful for these methods. In particular, the compound is an optically active atropisomer of 2-((6-amino-9H-purin-9-yl)methyl)-5-methyl-3-o-tolylquinazolin-4(3H)-one.
Claims16
An optically active compound comprising an atropisomer of formula 1(S)
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein the atropisomer of formula 1(S) is present in excess of its corresponding enantiomer of formula 1(R)
An optically active compound comprising an atropisomer of formula 1(R)
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein the atropisomer of formula 1(R) is present in excess of its corresponding enantiomer of formula 1(S)
A method of treating a condition in a human, wherein the condition is selected from the group consisting of allergic rhinitis, asthma, atopic dermatitis, chronic obstructive pulmonary disease (COPD), multiple sclerosis (MS), rheumatoid arthritis (RA), and diabetes,
- which comprises administering to a human in need thereof a therapeutically effective amount of an optically active atropisomer having the formula
- or a pharmaceutically acceptable salt thereof.
A method of treating cancer in a human, wherein the cancer is leukemia, lymphoma, or multiple myeloma, which comprises administering to a human in need thereof a therapeutically effective amount of an optically active atropisomer having the formula
- or a pharmaceutically acceptable salt thereof.
An optically active atropisomer obtained by separation of a racemic mixture of formula 1
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein the optically active atropisomer is characterized by a shorter retention time on a normal phase chiral column when compared to its enantiomer.
An optically active atropisomer obtained by separation of a racemic mixture of formula 1
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein the optically active atropisomer is characterized by a longer retention time on a normal phase chiral column when compared to its enantiomer.
Dependencies are inferred from the claim text.