IP Library Granted Patent US 9,566,283
Granted Patent B2
US 9,566,283 · App. 14/793,506 · Granted Feb 14, 2017

Compositions and methods for inhibition of the JAK pathway

Inventors: Yan Chen (Foster City, CA); Vanessa Taylor (San Francisco, CA); Hui Li (Santa Clara, CA); Rajinder Singh (Belmont, CA)
Assignee: Rigel Pharmaceuticals, Inc.
A61K31/5415A61K31/155A61K31/506A61K31/538A61K31/5377A61K31/5383A61K31/54A61K31/541A61K31/55A61K31/551A61K31/675A61K45/06C07D401/14C07D403/12C07D413/04C07D413/12C07D413/14C07D419/14C07D471/04C07D471/08C07D487/04C07D487/08C07D487/10C07D491/08C07D498/04C07F9/65583
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Quick Facts
Patent No.
US 9,566,283
App. No.
14/793,506
Granted
Feb 14, 2017
Kind
B2
Abstract

Disclosed are compounds of formula I, compositions containing them, and methods of use for the compounds and compositions in the treatment of conditions in which modulation of the JAK pathway or inhibition of JAK kinases, particularly JAK 2 and JAK3, are therapeutically useful.

Claims (12)

1. A method, comprising administering to a subject an amount of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or a salt thereof, or a composition compromising 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one or salt thereof, effective to contact a JAK kinase and inhibit a property thereof.

2. The method according to claim 1 , comprising administering 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one in an amount effective for treating a disease selected from allergies, autoimmune diseases, transplant rejection, T-cell mediated autoimmune diseases, Type II inflammatory diseases, delayed Type IV hypersensitivity reactions, or hematologic malignancies.

3. The method according to claim 1 comprising administering 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or a salt thereof, in combination with or adjunctively to a second therapeutic.

4. The method according to claim 3 , wherein the second therapeutic is a corticosteroid, an alkylating agent, a calcineurin inhibitor, an inhibitor of inosine monophosphate dehydrogenase (IMPDH), an agent designed to suppress cellular immunity while leaving the recipient's humoral immunologic response intact, a Syk kinase inhibitor, or a combination thereof.

5. The method according to claim 3 , wherein the second therapeutic is mercaptopurine, prednisone, methylprednisolone, prednisolone, cyclophosphamide, cyclosporine, sirolimus, tacrolimus, mycophenolate, mycophenolate mofetil, azathioprine, antilymphocyte globulin (ALG), antithymocyte globulin (ATG), monoclonal anti-T-cell antibodies (OKT3)), irradiation, or a combination thereof.

6. The method according to claim 1 comprising administering to the subject a hydrochloride salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or administering to the subject a composition compromising the hydrochloride salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one.

7. The method according to claim 1 comprising administering to the subject a benzene sulfonic acid salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or administering to the subject a composition compromising the benzene sulfonic acid salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one.

8. A method, comprising contacting a JAK kinase with 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or a salt thereof, or a composition compromising 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one or salt thereof, in an amount effective to inhibit an activity of the JAK kinase.

9. The method according to claim 8 , comprising contacting the JAK kinase ex vivo.

10. The method according to claim 8 , comprising contacting the JAK kinase in vivo.

11. The method according to claim 8 comprising contacting the JAK kinase with a hydrochloride salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or contacting the JAK kinase with a composition compromising the hydrochloride salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one.

12. The method according to claim 8 comprising contacting the JAK kinase with a benzene sulfonic acid salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one, or contacting the JAK kinase with a composition compromising the benzene sulfonic acid salt of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one.

Assignments (3)
SECURITY INTEREST Recorded Aug 25, 2022
From: RIGEL PHARMACEUTICALS, INC.
To: MIDCAP FINANCIAL TRUST
Reel/Frame 061327/0712 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2015
From: CHEN, YAN; TAYLOR, VANESSA; LI, HUI; SINGH, RAJINDER
To: RIGEL PHARMACEUTICALS, INC.
Reel/Frame 036301/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2015
From: CHEN, YAN; TAYLOR, VANESSA; LI, HUI; SINGH, RAJINDER
To: RIGEL PHARMACEUTICALS, INC.
Reel/Frame 036301/0395 →
Continuity (7)
Continuation 14250329 · Apr 10, 2014
Continuation 14023158 · Sep 10, 2013
Continuation 13283471 · Oct 27, 2011
Continuation 12692493 · Jan 22, 2010
Provisional Application 61241630 · Sep 11, 2009
Provisional Application 61147059 · Jan 23, 2009
Related Publication 20150307515A1 · Oct 29, 2015