# US 10,766,879 B2 · Pyrimidine derivatives as kinase inhibitors and their therapeutical applications

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- Number: US 10,766,879 B2
- Document ID: US10766879B2
- Status: Granted
- Kind: B2
- Application number: 15/553,890
- Filed: 2015-02-27
- Published: 2018-06-07
- Granted: 2020-09-08
- Earliest claimed: 2015-02-27
- Assignees: NantBioScience, Inc.
- Applicants: NantBioScience, Inc.
- Inventors: Chunlin Tao; Qinwei Wang; Laxman Nallan; David Ho; Tulay Polat; Forrest Arp; Paul Weingarten
- Web page: https://patentgrep.com/patent/US10766879B2

## CPC

- C07D 403/12: linked by a chain containing hetero atoms as chain links
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 487/04: 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

The present invention provides antitumor agents comprising substituted pyrimidine derivatives and pharmaceutically-acceptable formulations thereof, methods for making novel compounds and methods for using the compounds. The compounds and compositions in accordance with the invention have utility in treatment of a variety of diseases and have kinase inhibitory activities.

## Claims

### Claim 1

A compound of the formula
or a pharmaceutically acceptable salt thereof, wherein:
W is selected from the group consisting of: Cl, Br, I, CN, and CONH2;
Ar represents heteroaryl or aryl, each of which is substituted with from 0 to 4 substituents independently chosen from the group consisting of:
(1) halogen, hydroxy, amino, amide, cyano, —COOH, —SO2NH2, oxo, nitro or alkoxycarbonyl;
(2) NR1; and
(3) groups of the formula
wherein:
R1 represents hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, alkylthio, aryl, or arylalkyl;
R4 represents hydrogen, C1-C4 alkyl, or oxo;
X—R3 is CH; or X—R3 is O; or X is N, and R3 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 aryl or heteroaryl, (C3-C7 cycloalkyl)C1-C4 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C2-C6 alkanoyl, C1-C6 alkoxycarbonyl, C2-C6 alkanoyloxy, mono- and di-(C3-C8 cycloalkyl)aminoC0-C4alkyl, (4- to 7-membered heterocycle)C0-C4alkyl, C1-C6 alkylsulfonyl, mono- and di-(C1-C6 alkyl) sulfonamido, and mono- and di-(C1-C6 alkyl)aminocarbonyl, each of which is substituted with from 0 to 4 substituents independently chosen from halogen, hydroxy, cyano, amino, —COOH or oxo;
R5 and R6 are independently selected from the group consisting of: hydrogen, F, Cl, and Br; and
R7, R8 and R9 are independently selected from the group consisting of: hydrogen and CH3.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising at least one compound of claim 1 or its pharmaceutically acceptable salts, hydrates, solvates, crystal forms salts and individual diastereomers thereof, and a pharmaceutically acceptable carrier.

### Claim 3 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein W is CN.

### Claim 4 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein R5 and R6 are each F.

### Claim 5 (depends on 3)

The compound or the pharmaceutically acceptable salt thereof according to claim 3, wherein R5 and R6 are each F.

### Claim 6 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein R8 is CH3.

### Claim 7 (depends on 5)

The compound or the pharmaceutically acceptable salt thereof according to claim 5, wherein R8 is CH3.

### Claim 8 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein R7 and R9 are each H.

### Claim 9 (depends on 7)

The compound or the pharmaceutically acceptable salt thereof according to claim 7, wherein R7 and R9 are each H.