IP Library Granted Patent US 11,229,630
Granted Patent B2
US 11,229,630 · App. 16/852,272 · Granted Jan 25, 2022

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 11,229,630
App. No.
16/852,272
Granted
Jan 25, 2022
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 (32)

1. A method of preventing recurrence of a cancer in a patient comprising administering to the patient 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 or C 1 -C 6 alkyl.

2. The method of claim 1 , wherein the cancer is selected from breast cancer, ovarian cancer, endometrial cancer, vaginal cancer, lung cancer, bone cancer, uterine cancer and endometriosis.

3. The method of claim 1 , wherein the compound is administered as an adjunctive therapy after or instead of chemotherapy, radiation, or surgery.

4. The method of claim 3 , wherein the compound is administered after surgery.

5. The method of claim 1 , wherein the compound is administered prior to surgery.

6. The method of claim 2 , wherein the cancer is breast cancer.

7. The method of claim 6 , wherein the breast cancer has progressed in the presence of endocrine or aromatase therapy.

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

9. The method of claim 1 , wherein Y is

10. The method of claim 1 , wherein Y is

11. The method of claim 1 , wherein R 5 is C 1 -C 6 [[ ]]alkyl or C 1 -C 6 [[ ]]haloalkyl.

12. The method of claim 1 , wherein R 7 and R 8 are each independently selected from hydrogen or C 1 -C 6 alkyl.

13. The method of claim 1 , wherein the compound is of Formula I(a):

or a pharmaceutically acceptable salt thereof.

14. The method of claim 13 , wherein R 1 , R 2 , R 3 and R 4 are each hydrogen.

15. The method of claim 1 , wherein the compound is of Formula I(c):

or a pharmaceutically acceptable salt thereof.

16. The method of claim 15 , wherein R 1 , R 2 , R 3 and R 4 are each hydrogen.

17. The method of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

18. The method of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

19. The method of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2020
From: MYLES, DAVID C.; KUSHNER, PETER J.; HARMON, CYRUS L.
To: OLEMA PHARMACEUTICALS, INC.
Reel/Frame 053795/0317 →
Continuity (4)
Continuation 16391686 · Apr 23, 2019
Continuation 15764988
Provisional Application 62235900 · Oct 1, 2015
Related Publication 20210059991A1 · Mar 4, 2021
Cited By (1)
US 12,370,181