# US 11,028,101 B2 · 3-oxa-8-azabicyclo[3.2.1]octane derivatives and their use in the treatment of cancer and hemoglobinopathies

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- Number: US 11,028,101 B2
- Document ID: US11028101B2
- Status: Granted
- Kind: B2
- Application number: 16/687,401
- Filed: 2019-11-18
- Published: 2020-03-19
- Granted: 2021-06-08
- Earliest claimed: 2016-03-09
- Assignees: Ctxt Pty Ltd
- Applicants: Ctxt Pty Ltd
- Inventors: Paul Anthony Stupple
- Web page: https://patentgrep.com/patent/US11028101B2

## CPC

- C07D 498/08: Bridged systems
- A61K 31/5386: spiro-condensed or forming part of bridged ring systems
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 7/06: Antianaemics
- A61P 35/00: Antineoplastic agents
- C07D 217/16: substituted by oxygen atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound of formula Ia, Ib, Ic or Id: wherein: n is 1 or 2; RN is H or Me; R1 is optionally one or more halo or methyl groups; R2a and R2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2c and R2d (if present) are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R3a and R3b are independently selected from H and Me; R4a is selected from OH, —NH2, —C(═O)NH2, and —CH2OH; R4b is either H or Me; R5 is either H or Me; m is 1 or 2; q is 0 or 1; R11a, R11b, R11c and R11d are independently selected from H, halo, C1-4 alkyl, C1-4 fluoroalkyl, C3-4 cycloalkyl, C1-4 alkyloxy, NH—C1-4 alkyl and cyano; R12a and R12b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R12c and R12d are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R12e is H or Me; R13a and R13b are independently selected from H and Me; R14 is either H or Me; R16a and R16b are independently selected from H and Me; R6 is selected from H, OMe, and OEt.

## Claims

### Claim 1

A compound of formula:

### Claim 2

A method for the treatment of cancer, comprising administering to a patient in need of treatment, a therapeutically effective PRMT5 activity inhibiting amount of a composition comprising a compound of the following formula:
or pharmaceutically acceptable salts thereof; and a pharmaceutical carrier;
wherein the cancer is any one or more of the following: leukemia, acute lymphocytic leukemia (ALL), acute myeloid leukemia (AML), chronic lymphocytic leukemia (CLL), chronic myeloid leukemia (CML), non-Hodgkin's lymphoma, Hodgkin's disease, prostate cancer, lung cancer, melanoma, breast cancer, colon and rectal cancer, colon cancer, squamous cell carcinoma and gastric cancer.