IP Library Granted Patent US 9,738,624
Granted Patent B2
US 9,738,624 · App. 14/900,469 · Granted Aug 22, 2017

Nuclear transport modulators and uses thereof

Inventors: Erkan Baloglu (Stoneham, MA); Sharon Shacham (Newton, MA); Dilara McCauley (Arlington, MA); Trinayan Kashyap (Framingham, MA); William Senapedis (Millis, MA); Yosef Landesman (Brookline, MA); Gali Golan (Mesilat Zion, IL); Ori Kalid (Pardes Hanna, IL); Sharon Shechter (Andover, MA)
Assignee: Karyopharm Therapeutics Inc.
C07D401/06C07D249/08C07D403/06C07D405/06C07D413/06C07D417/06
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Quick Facts
Patent No.
US 9,738,624
App. No.
14/900,469
Granted
Aug 22, 2017
Kind
B2
Abstract

The present invention relates to compounds of formula (I): and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising the compounds of formula (I) or their pharmaceutically acceptable salts, and methods of using said compounds, salts and compositions in the treatment of various disorders associated with CRM1 activity.

Claims (25)

1. A compound represented by structural formula IV:

or a pharmaceutically acceptable salt thereof, wherein:

R 2 is selected from optionally substituted heteroaryl having 5 to 15 ring atoms and optionally substituted aryl having 6 to 12 ring atoms.

2. The compound of claim 1 , wherein R 2 is an optionally substituted heteroaryl having 5 to 15 ring atoms.

3. The compound of claim 2 , wherein R 2 is an optionally substituted 5-6-membered heteroaryl having 1, 2 or 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur.

4. The compound of claim 3 , wherein R 2 is an optionally substituted 5-membered heteroaryl having 1, 2 or 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur.

5. The compound of claim 4 , wherein R 2 is an optionally substituted pyrrolyl, furanyl, thiophenyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, or oxadiazolyl.

6. The compound of claim 3 , wherein R 2 is an optionally substituted 6-membered heteroaryl having 1, 2 or 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur.

7. The compound of claim 6 , wherein R 2 is an optionally substituted pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl.

8. The compound of claim 1 , wherein R 2 is optionally substituted with 1, 2 or 3 substituents independently selected from halogen, C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 thioalkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, sulfhydryl, cyano, C 6 aryl and heteroaryl having 5 or 6 ring atoms.

9. The compound of claim 8 , wherein R 2 is optionally substituted with 1, 2 or 3 substituents independently selected from fluoro, chloro, C 1 -C 4 alkyl, —CF 3 , amino and cyano.

10. A compound of claim 1 , represented by any one of the following structural formulas:

or a pharmaceutically acceptable salt of any of the foregoing.

11. The compound of claim 10 , selected from:

or a pharmaceutically acceptable salt of any of the foregoing, wherein the exocyclic double bond is in a trans configuration.

12. The compound of claim 10 , selected from:

or a pharmaceutically acceptable salt of any of the foregoing, wherein the exocyclic double bond is in a cis configuration.

13. A pharmaceutically acceptable composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

14. A method for promoting wound healing in a subject in need thereof, comprising administering to the subject in need thereof a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1 represented by the following structural formula

or a pharmaceutically acceptable salt thereof.

16. A method of treating multiple myeloma in a subject in need thereof comprising administering to the subject in need thereof a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

17. A method of treating a leukemia in a subject in need thereof comprising administering to the subject in need thereof a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the leukemia is selected from: hairy cell leukemia, acute lymphoblastic leukemia, chronic myelogenous leukemia, acute myeloid leukemia and chronic lymphocytic leukemia.

18. A method of treating a lymphoma in a subject in need thereof comprising administering to the subject in need thereof a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the lymphoma is selected from: cutaneous T-Cell lymphoma; diffuse large B-cell lymphoma; mantle cell lymphoma; and follicular lymphoma.

19. A method of treating a solid cancer in a subject in need thereof comprising administering to the subject in need thereof a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the solid cancer is selected from: prostate cancer; breast cancer; liver cancer; colon cancer; pancreatic cancer; renal cancer; and ovarian cancer.

Assignments (6)
RELEASE OF SECURITY INTEREST IN PATENTS AT REEL/FRAME NO. 67396/0532 Recorded Oct 14, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS AGENT
To: KARYOPHARM THERAPEUTICS INC.
Reel/Frame 073111/0142 →
PATENT SECURITY AGREEMENT Recorded Oct 10, 2025
From: KARYOPHARM THERAPEUTICS INC.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS COLLATERAL TRUSTEE
Reel/Frame 073058/0504 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded May 13, 2024
From: KARYOPHARM THERAPEUTICS INC.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 067396/0532 →
SECURITY INTEREST Recorded May 8, 2024
From: KARYOPHARM THERAPEUTICS INC.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 067345/0255 →
NOTICE OF SECURITY INTEREST IN PATENTS Recorded Sep 27, 2019
From: KARYOPHARM THERAPEUTICS INC.
To: HCR COLLATERAL MANAGEMENT, LLC
Reel/Frame 050575/0574 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2017
From: SHACHAM, SHARON; MCCAULEY, DILARA; KASHYAP, TRINAYAN; SENAPEDIS, WILLIAM; LANDESMAN, YOSEF; GOLAN, GALI; KALID, ORI; SHECHTER, SHARON; BALOGLU, ERKAN
To: KARYOPHARM THERAPEUTICS INC.
Reel/Frame 042554/0400 →
Continuity (2)
Provisional Application 61838172 · Jun 21, 2013
Related Publication 20160152596A1 · Jun 2, 2016