IP Library › Granted Patent US 10,399,979
Granted Patent B2
US 10,399,979 · App. 16/175,915 · Granted Sep 3, 2019

Janus kinase inhibitors and uses thereof

Inventors: Mark Stanley Cushman (West Lafayette, IN); Mohamed S. A. Elsayed (West Lafayette, IN)
Assignee: Purdue Research Foundation
C07D471/14A61K31/4745
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Quick Facts
Patent No.
US 10,399,979
App. No.
16/175,915
Granted
Sep 3, 2019
Kind
B2
Abstract

The invention described herein pertains to selective Janus kinase (JAK) inhibitors and methods of use thereof. Also described are methods for treating diseases involved abnormal JAK/STAT signaling pathway in mammals using the described selective JAK inhibitors or a pharmaceutical formulation thereof.

Claims (29)

1. A compound having the formula (I)

or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein

R 1 is an alkyl, alkenyl, heteroalkyl, heteroalkenyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, arylalkyl, and arylalkenyl, each of which is optionally substituted;

R 2 represent four substituents each independently selected from the group consisting of hydrogen, halo, azido, cyano, nitro, hydroxy, amino, thio, and derivatives thereof; or any two adjacent substituents that are taken together with the attached carbons to form an optionally substituted heterocycle, and each of other two substituents is defined as above;

R 3 represent two substituents each independently selected from the group consisting of hydrogen, halo, azido, cyano, nitro, hydroxy, amino, thio, and derivatives thereof; and

R 4 is hydrogen, an alkyl, alkenyl, heteroalkyl, heteroalkenyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, arylalkyl, and arylalkenyl, each of which is optionally substituted.

2. The compound according to claim 1 , wherein the compounds are:

3. The compound according to claim 1 , wherein R 1 is a C3-C8 alkyl, alkenyl, cycloalkyl, cycloalkenyl, and heterocyclyl, each of which is optionally substituted.

4. The compound according to claim 3 , wherein R 1 is an optionally substituted C3-C8 cycloalkyl.

5. The compound according to claim 1 , wherein R 3 and R 4 are hydrogen.

6. The compound according to claim 1 , wherein the compound has the formula (II),

wherein R 1 is a C1-C12 alkyl, alkenyl, heteroalkyl, heteroalkenyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, arylalkyl, and arylalkenyl, each of which is optionally substituted.

7. The compound according to claim 6 , wherein R 1 is a C3-C8 alkyl, alkenyl, cycloalkyl, cycloalkenyl, and heterocyclyl, each of which is optionally substituted.

8. The compound according to claim 7 , wherein R 1 is an optionally substituted C3-C8 cycloalkyl.

9. The compound according to claim 6 , wherein R 3 and R 4 are hydrogen.

10. The compound according to claim 6 , wherein the compounds are:

11. A pharmaceutical composition comprising one or more compounds of claim 1 , or a pharmaceutically acceptable salt thereof, together with one or more diluents, excipients or carriers.

12. A pharmaceutical composition comprising one or more compounds of claim 1 , or a pharmaceutically acceptable salt thereof, together with one or more diluents, excipients or carriers, for use in the treatment of a cancer, wherein said cancer comprises leukemia, non-small cell lung cancer (NSCLC), colon cancer, central neuro system (CNS) cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer.

13. A pharmaceutical composition comprising one or more compounds of claim 1 , or a pharmaceutically acceptable salt thereof, and one or more other therapeutic compounds, together with one or more diluents, excipients or carriers, for use in the treatment of a cancer, wherein said cancer comprises leukemia, non-small cell lung cancer (NSCLC), colon cancer, central neuro system (CNS) cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer.

14. A method for treating a cancer, wherein said cancer comprises leukemia, non-small cell lung cancer (NSCLC), colon cancer, central neuro system (CNS) cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer, comprising the step of administering a therapeutically effective amount of one or more compounds of claim 1 , and one or more carriers, diluents, or excipients, to a patient in need of relief from said cancer.

15. A method for treating a cancer, wherein said cancer comprises leukemia, non-small cell lung cancer (NSCLC), colon cancer, central neuro system (CNS) cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer, comprising the step of administering a therapeutically effective amount of a compound of claim 1 in combination with one or more other compounds of the same or different mode of action, and one or more carriers, diluents, or excipients, to a patient in need of relief from said cancer.

16. A method for treating diseases mediated by abnormal JAK/STAT signaling pathway, such as inflammation, cancer, viral and bacterial infections, neurological and immunological disorders, wherein said cancer comprises leukemia, non-small cell lung cancer (NSCLC), colon cancer, central neuro system (CNS) cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer, comprising the step of administering a therapeutically effective amount of one or more compounds of formula (I), and one or more carriers, diluents, or excipients, to a patient in need of relief from said disease:

or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein

R 1 is an alkyl, alkenyl, heteroalkyl, heteroalkenyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, arylalkyl, and arylalkenyl, each of which is optionally substituted;

R 2 represent four substituents each independently selected from the group consisting of hydrogen, halo, azido, cyano, nitro, hydroxy, amino, thio, and derivatives thereof; or any two adjacent substituents that are taken together with the attached carbons to form an optionally substituted heterocycle, and each of other two substituents is defined as above;

R 3 represent two substituents each independently selected from the group consisting of hydrogen, halo, azido, cyano, nitro, hydroxy, amino, thio, and derivatives thereof; and

R 4 is hydrogen, an alkyl, alkenyl, heteroalkyl, heteroalkenyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, arylalkyl, and arylalkenyl, each of which is optionally substituted.

17. The method according to claim 16 , wherein R 1 is a C3-C8 alkyl, alkenyl, cycloalkyl, cycloalkenyl, and heterocyclyl, each of which is optionally substituted.

18. The method according to claim 16 , wherein R 3 and R 4 are hydrogen.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2019
From: CUSHMAN, MARK S.; ELSAYED, MOHAMED S.A.
To: PURDUE RESEARCH FOUNDATION
Reel/Frame 049754/0511 →
Continuity (2)
Provisional Application 62579327 · Oct 31, 2017
Related Publication 20190127377A1 · May 2, 2019