IP Library Granted Patent US 10,624,878
Granted Patent B2
US 10,624,878 · App. 16/391,686 · Granted Apr 21, 2020

Tetrahydro-1H-pyrido [3,4-b]indole anti-estrogenic drugs

Inventors: David C. Myles (Berkeley, CA); Peter J. Kushner (San Francisco, CA); Cyrus L. Harmon (Bolinas, CA)
Assignee: Olema Pharmaceuticals, Inc.
A61K31/437A61K31/4545A61K31/475A61K31/506A61K45/06A61P35/00C07D471/04
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Quick Facts
Patent No.
US 10,624,878
App. No.
16/391,686
Granted
Apr 21, 2020
Kind
B2
Abstract

The present disclosure provides tetrahydro-1H-pyrido[3,4-b]indole compounds or a pharmaceutically acceptable salt, solvate, hydrate, prodrug, stereoisomer, tautomer, rotamer, N-oxide and/or substituted derivative or, optionally in a pharmaceutical composition, for the modulation of disorders mediated by estrogen, or other disorders as more fully described herein.

Claims (38)

1. A method of treating a subject suffering from a cancer comprising administering a compound of Formula I:

or a pharmaceutically acceptable salt thereof,

wherein:

X is —CH 2 - or —O—;

Y is

R 1 and R 2 are each hydrogen;

R 3 and R 4 are each independently selected from hydrogen and halo, and when one of R 3 or R 4 is halo, the other of R 3 or R 4 is hydrogen;

R 5 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 0 -C 4 (C 3 -C 6 cycloalkyl), or C 1 -C 6 heteroalkyl;

R 6 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or C 0 -C 4 (C 3 -C 6 cycloalkyl); and

R 7 and R 8 are each independently selected from hydrogen and C 1 -C 6 alkyl;

in combination with an anti-cancer agent.

2. The method of claim 1 , wherein the anti-cancer agent is selected from an mTOR inhibitor, a CDK4/6 inhibitor, a PI3 kinase inhibitor, an aromatase inhibitor, an antibody to or inhibitor of PD-1, PD-L1 or CTLA-4, or an antibody to or inhibitor of EGFR, PGFR, or IGFR.

3. The method of claim 2 , wherein the anti-cancer agent is an mTOR inhibitor.

4. The method of claim 3 , wherein the mTOR inhibitor is selected from everolimus and rapamycin.

5. The method of claim 2 , wherein the anti-cancer agent is a CDK4/6 inhibitor.

6. The method of claim 5 , wherein the CDK4/6 inhibitor is selected from palbociclib, abemaciclib and ribociclib.

7. The method of claim 2 , wherein the anti-cancer agent is an antibody to or inhibitor of PD-1, PD-L1 or CTLA-4.

8. The method of claim 2 , wherein the anti-cancer agent is an antibody to or inhibitor of EGFR, PGFR, or IGFR.

9. The method of claim 1 , wherein the anti-cancer agent is selected from trastuzumab, pertuzumab, ado-trastuzumab, trastuzumab emtansine, erlotinib, gefitinib, and neratinib.

10. The method of claim 2 , wherein the anti-cancer agent is a PI3 kinase inhibitor.

11. The method of claim 10 , wherein the PI3 kinase inhibitor is selected from perifosine, CAL101, BEZ235, XL147, XL765, GDC-0941, and IPI-145.

12. The method of claim 2 , wherein the anti-cancer agent is an aromatase inhibitor.

13. The method of claim 12 , wherein the aromatase inhibitor is selected from aminoglutethimide, testolactone, anastrozole, letrozole, exemestane, vorozole, formestane, fadrozole, 4-hydroxyandrostenedione, 1,4,6-androstatrien-3, 17-dione, and 4-androstene-3,6, 17-trione.

14. The method of claim 12 , wherein the aromatase inhibitor is selected from anastrozole, letrozole, and exemestane.

15. The method of claim 1 , wherein X is —O—.

16. The method of claim 1 , wherein Y is

17. The method of claim 1 , wherein Y is

18. The method of claim 16 , wherein R 5 is C 1 -C 6 alkyl.

19. The method of claim 17 , wherein R 5 is C 1 -C 6 haloalkyl.

20. The method of claim 1 , wherein R 6 is C 1 -C 6 haloalkyl.

21. The method of claim 1 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

22. The method of claim 21 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

23. The method of claim 21 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

24. The method of claim 21 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2019
From: MYLES, DAVID C.; KUSHNER, PETER J.; HARMON, CYRUS L.
To: OLEMA PHARMACEUTICALS, INC.
Reel/Frame 050992/0946 →
Continuity (3)
Continuation 15764988
Provisional Application 62235900 · Oct 1, 2015
Related Publication 20190247372A1 · Aug 15, 2019
Cited By (1)
US 12,370,181