# US 11,299,493 B2 · Heterocyclic compounds and uses thereof

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- Number: US 11,299,493 B2
- Document ID: US11299493B2
- Status: Granted
- Kind: B2
- Application number: 16/155,838
- Filed: 2018-10-09
- Published: 2019-04-11
- Granted: 2022-04-12
- Earliest claimed: 2017-10-09
- Assignees: Nuvation Bio Inc.
- Applicants: Nuvation Bio Inc.
- Inventors: Sarvajit Chakravarty; Son Minh Pham; Jayakanth Kankanala; Anil Kumar Agarwal; Brahmam Pujala; Sanjeev Soni; Satish K. Arya; Deepak Palve; Ashu Gupta; Varun Kumar
- Web page: https://patentgrep.com/patent/US11299493B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- C07D 471/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Heterocyclic compounds as Wee1 inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

## Claims

### Claim 1

A compound of the Formula (Ia-9):
or a pharmaceutically acceptable salt thereof, wherein:
R2 is C1-C6 alkyl or C3-C6 cycloalkyl;
Y is hydrogen or R4;
n and p are independently 0, 1, 2, 3, or 4;
each R3a is independently C1-C6 alkyl optionally substituted by oxo, —OH or halogen;
each R4 is independently C1-C6 alkyl,
or two R4, when bound to the same carbon or two different carbon atoms, are taken together with the carbon or carbons to which they are attached to form a C3-C6 cycloalkyl.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein n is 0.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein n is 1.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein n is 2.

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein Y is hydrogen.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein each R4 is methyl.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is C1-C6 alkyl.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is isopropyl.

### Claim 9 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is C3-C6 cycloalkyl.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is cyclopropyl.

### Claim 11 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R3a and the pyridin-4-yl are taken together to form a moiety selected from the group consisting of:

### Claim 12 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein p is 1.

### Claim 13 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of

### Claim 14 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of

### Claim 15 (depends on 14)

The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 16 (depends on 14)

The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 17 (depends on 14)

The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 18 (depends on 14)

The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 19

A compound of the Formula (Ia-7):
or a pharmaceutically acceptable salt thereof, wherein:
R2 is isopropyl or C3-C6 cycloalkyl;
Y is hydrogen or R4;
n and p are independently 0, 1, 2, 3, or 4;
each R3a is independently C1-C6 alkyl optionally substituted by oxo, —OH or halogen;
each R4 is independently C1-C6 alkyl,
or two R4, when bound to the same carbon or two different carbon atoms, are taken together with the carbon or carbons to which they are attached to form a C3-C6 cycloalkyl.

### Claim 20 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein n is 0.

### Claim 21 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein n is 1.

### Claim 22 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein n is 2.

### Claim 23 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein Y is hydrogen.

### Claim 24 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein each R4 is methyl.

### Claim 25 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein R2 is isopropyl.

### Claim 26 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein R2 is C3-C6 cycloalkyl.

### Claim 27 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein R2 is cyclopropyl.

### Claim 28 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein R3a and the pyridin-4-yl are taken together to form a moiety selected from the group consisting of:

### Claim 29 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein p is 1.

### Claim 30 (depends on 19)

A pharmaceutical composition comprising the compound of claim 19, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

### Claim 31 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of

### Claim 32 (depends on 19)

The compound of claim 19, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of

### Claim 33 (depends on 32)

The compound of claim 32, or a pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 34 (depends on 32)

The compound of claim 32, or a pharmaceutically acceptable salt thereof, wherein the compound is