IP Library Granted Patent US 11,065,236
Granted Patent B2
US 11,065,236 · App. 16/557,025 · Granted Jul 20, 2021

Pharmaceutical compositions containing a PDE4 inhibitor and a PI3 delta or dual PI3 delta-gamma kinase inhibitor

Inventors: Swaroop K. Vakkalanka (La Chaux-de-Fonds, CH); Srikant Viswanadha (Hyderabad, IN)
Assignee: Rhizen Pharmaceuticals SA
A61K31/44A61K31/519A61K31/52A61K45/06A61K2300/00
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Quick Facts
Patent No.
US 11,065,236
App. No.
16/557,025
Granted
Jul 20, 2021
Kind
B2
Abstract

This present invention relates to a method of treating a autoimmune, respiratory and/or inflammatory disease or condition (e.g., psoriasis, rheumatoid arthritis, asthma, COPD). The method comprises administering a PI3K Delta inhibitor or a dual PI3K Delta-Gamma inhibitor and a PDE4 inhibitor. The present invention also relates to pharmaceutical compositions containing a PI3K Delta or dual PI3K Delta-Gamma inhibitor and a PDE4 inhibitor.

Claims (16)

1. A method of treating an autoimmune, respiratory and/or inflammatory disease or condition, the method comprising administering to a subject in need thereof a therapeutically effective amount of (i) a PI3K Delta inhibitor or a dual PI3K Delta and Gamma inhibitor, and (ii) a PDE4 inhibitor, wherein

(a) the PI3K Delta inhibitor is selected from (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, (S)-2-(1-(9H-purin-6-ylamino)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one, 2-((6-amino-9H-purin-9-yl)methyl)-5-methyl-3-o-tolylquinazolin-4(3H)-one, (S)-2-(1-((9H-purin-6-yl)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one, and pharmaceutically acceptable salts thereof,

(b) the dual PI3K Delta and Gamma inhibitor is selected from (+)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one, (S)-3-(1-(9H-purin-6-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one, and pharmaceutically acceptable salts thereof, and

(c) the PDE4 inhibitor is selected from roflumilast and apremilast.

2. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from (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 and pharmaceutically acceptable salts thereof, and (ii) roflumilast.

3. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from (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 and pharmaceutically acceptable salts thereof, and (ii) apremilast.

4. The method of claim 1 , the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from (S)-2-(1-(9H-purin-6-ylamino)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one and pharmaceutically acceptable salts thereof, and (ii) roflumilast.

5. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from (S)-2-(1-(9H-purin-6-ylamino)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one and pharmaceutically acceptable salts thereof, and (ii) apremilast.

6. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from 2-((6-amino-9H-purin-9-yl)methyl)-5-methyl-3-o-tolylquinazolin-4(3H)-one and pharmaceutically acceptable salts thereof, and (ii) roflumilast.

7. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from 2-((6-amino-9H-purin-9-yl)methyl)-5-methyl-3-o-tolylquinazolin-4(3H)-one and pharmaceutically acceptable salts thereof, and (ii) apremilast.

8. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from (S)-2-(1-((9H-purin-6-yl)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one and pharmaceutically acceptable salts thereof, and (ii) roflumilast.

9. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a PI3K Delta inhibitor selected from (S)-2-(1-((9H-purin-6-yl)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one and pharmaceutically acceptable salts thereof, and (ii) apremilast.

10. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a dual PI3K Delta and Gamma inhibitor selected from (+)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one and pharmaceutically acceptable salts thereof, and (ii) roflumilast.

11. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a dual PI3K Delta and Gamma inhibitor selected from (+)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one and pharmaceutically acceptable salts thereof, and (ii) apremilast.

12. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a dual PI3K Delta and Gamma inhibitor selected from (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one and pharmaceutically acceptable salts thereof, and (ii) roflumilast.

13. The method of claim 1 , wherein the method comprises administering to the subject a therapeutically effective amount of (i) a dual PI3K Delta and Gamma inhibitor selected from (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one and pharmaceutically acceptable salts thereof, and (ii) apremilast.

Assignments (2)
CHANGE OF ADDRESS Recorded Oct 6, 2021
From: RHIZEN PHARMACEUTICALS AG
To: RHIZEN PHARMACEUTICALS AG
Reel/Frame 057836/0286 →
CHANGE OF ADDRESS Recorded Mar 22, 2021
From: RHIZEN PHARMACEUTICALS SA
To: RHIZEN PHARMACEUTICALS SA
Reel/Frame 056775/0375 →
Priority Claims (2)
IN 2762/CHE/2012 · Nov 8, 2012 · national
IN 4688/CHE/2012 · Nov 8, 2012 · national
Continuity (4)
Continuation 16013607 · Jun 20, 2018
Continuation 15654181 · Jul 19, 2017
Continuation 14441758
Related Publication 20200237735A1 · Jul 30, 2020