# US 11,999,751 B2 · Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors

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- Number: US 11,999,751 B2
- Document ID: US11999751B2
- Status: Granted
- Kind: B2
- Application number: 17/409,976
- Filed: 2021-08-24
- Published: 2022-06-09
- Granted: 2024-06-04
- Earliest claimed: 2014-06-11
- Assignees: Incyte Corporation; Incyte Holdings Corporation
- Applicants: Incyte Corporation; Incyte Holdings Corporation
- Inventors: Yun-Long Li; Andrew P. Combs
- Web page: https://patentgrep.com/patent/US11999751B2

## CPC

- C07D 513/04: Ortho-condensed systems
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- C07D 471/04: Ortho-condensed systems
- 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

This application relates to derivatives of Formula I: and pharmaceutically acceptable salts thereof, which are inhibitors of PI3K, and compositions and methods of treatment related thereto.

## Claims

### Claim 1

A pharmaceutical composition comprising a compound selected from:
4-{3-chloro-6-ethoxy-2-fluoro-5-[1-([1,3]thiazolo[5,4-d]pyrimidin-7-ylamino)ethyl]phenyl}pyrrolidin-2-one;
4-{3-chloro-6-ethoxy-2-fluoro-5-[1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl]phenyl}pyrrolidin-2-one;
5-{3-chloro-6-methoxy-2-methyl-5-[(1S)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl]phenyl}-N,N-dimethylpyridine-2-carboxamide; and
4-chloro-N-ethyl-3′,5′-difluoro-3-methyl-6-[1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl]biphenyl-2-carboxamide;
or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1, wherein the compound is selected from:
(S)-4-(3-chloro-6-ethoxy-2-fluoro-5-((S)-1-(pyrido[3,2-d]pyrimidin-4-yl amino)ethyl)phenyl)pyrrolidin-2-one;
(R)-4-(3-chloro-6-ethoxy-2-fluoro-5-((R)-1-(pyrido[3,2-d] pyri mi di n-4-ylamino)ethyl)phenyl)pyrrolidin-2-one;
(S)-4-(3-chloro-6-ethoxy-2-fluoro-5-((R)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one; and
(R)-4-(3-chloro-6-ethoxy-2-fluoro-5-((S)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one;
or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1, wherein the compound is 4-{3-chloro-6-ethoxy-2-fluoro-5-[1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl]phenyl}pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 3)

The pharmaceutical composition of claim 3, wherein the compound is (S)-4-(3-chloro-6-ethoxy-2-fluoro-5-((S)-1-(pyri do[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 3)

The pharmaceutical composition of claim 3, wherein the compound is (R)-4-(3-chloro-6-ethoxy-2-fluoro-5-((R)-1-(pyri do[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 3)

The pharmaceutical composition of claim 3, wherein the compound is (S)-4-(3-chloro-6-ethoxy-2-fluoro-5-((R)-1-(pyri do[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 3)

The pharmaceutical composition of claim 3, wherein the compound is (R)-4-(3-chloro-6-ethoxy-2-fluoro-5-((S)-1-(pyri do[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 8

A compound, which is 4-{3-chloro-6-ethoxy-2-fluoro-5-[1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl]phenyl}pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 8)

The compound of claim 8, wherein the compound is (S)-4-(3-chloro-6-ethoxy-2-fluoro-5-((S)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 8)

The compound of claim 8, wherein the compound is (R)-4-(3-chloro-6-ethoxy-2-fluoro-5-((R)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 8)

The compound of claim 8, wherein the compound is (S)-4-(3-chloro-6-ethoxy-2-fluoro-5-((R)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 12 (depends on 8)

The compound of claim 8, wherein the compound is (R)-4-(3-chloro-6-ethoxy-2-fluoro-5-((S)-1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)phenyl)pyrrolidin-2-one, or a pharmaceutically acceptable salt thereof.