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Last Updated: April 29, 2024

Claims for Patent: 10,981,919


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Summary for Patent: 10,981,919
Title:Selective PI3K delta inhibitors
Abstract: The present invention relates to selective inhibitors of PI3K delta protein kinases, methods of preparing them, pharmaceutical compositions containing them and methods of treatment and/or prevention of kinase mediated diseases or disorders with them.
Inventor(s): Vakkalanka; Swaroop K. (La Chaux-de-Fonds, CH), Muthuppalaniappan; Meyyappan (Hyderabad, IN), Nagarathnam; Dhanapalan (Bethany, CT)
Assignee: Rhizen Pharmaceuticals SA (Basel, CH)
Application Number:16/776,327
Patent Claims: 1. (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]-p- yrimidin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one.

2. A pharmaceutical composition comprising a compound of claim 1 and at least one pharmaceutically acceptable carrier.

3. The pharmaceutical composition of claim 2, wherein the compound has an enantiomeric excess of at least 98%.

4. A method treating indolent non-Hodgkin's lymphoma in a human subject in need thereof comprising administering to the human subject an effective amount of (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)- 1H-pyrazolo [3,4-d]pyrimidin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one or a pharmaceutically acceptable salt thereof.

5. The method of claim 4, wherein an effective amount of (S)-2-(1-(4-amino -3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one 4-methylbenzenesulfonate is administered.

6. The method of claim 5, wherein the (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrim- idin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H -chromen-4-one 4-methylbenzenesulfonate has an enantiomeric excess of at least 95%.

7. The method of claim 5, wherein the (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrim- idin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H -chromen-4-one 4-methylbenzenesulfonate has an enantiomeric excess of at least 98%.

8. The method of claim 4, further comprising the step of administering simultaneously or sequentially to the subject at least one other anti-cancer agent.

9. A method of treating follicular lymphoma in a human subject in need thereof comprising administering to the human subject an effective amount of (S)-2-(1-(4-amino-3-(3-fluoro -4-isopropoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H -chromen-4-one or a pharmaceutically acceptable salt thereof.

10. The method of claim 9, wherein an effective amount of (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrim- idin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one 4-methylbenzenesulfonate is administered.

11. The method of claim 10, wherein the (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrim- idin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one 4-methylbenzenesulfonate has an enantiomeric excess of at least 95%.

12. The method of claim 10, wherein the (S)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrim- idin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H -chromen-4-one 4-methylbenzenesulfonate has an enantiomeric excess of at least 98%.

13. The method of claim 9, further comprising the step of administering simultaneously or sequentially to the subject at least one other anti-cancer agent.

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