# US 11,078,206 B2 · Amino-fluoropiperidine derivatives as kinase inhibitor

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- Number: US 11,078,206 B2
- Document ID: US11078206B2
- Status: Granted
- Kind: B2
- Application number: 16/770,642
- Filed: 2018-12-28
- Published: 2020-09-24
- Granted: 2021-08-03
- Earliest claimed: 2017-12-28
- Assignees: Daewoong Pharmaceutical Co., Ltd.
- Applicants: Daewoong Pharmaceutical Co., Ltd.
- Inventors: In Woo Kim; Seung Hwarn Jeong; Nam Youn Kim; Jun Hee Lee
- Web page: https://patentgrep.com/patent/US11078206B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to a compound represented by the following Chemical Formula 1, or a pharmaceutically acceptable salt thereof, and the compound according to the present invention can be usefully used for the prevention or treatment of diseases which are associated with kinase inhibitory actions.

## Claims

### Claim 1

A compound represented by the following Chemical Formula 1, or a pharmaceutically acceptable salt thereof:
wherein, in Chemical Formula 1,
R1 is C1-5 alkyl, halogen, or cyano,
X is N—R2, O, or S,
R2 is C1-5 alkyl, C1-5 haloalkyl, or C3-6 cycloalkyl.

### Claim 2 (depends on 1)

The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, bromo, chloro, fluoro, or cyano.

### Claim 3 (depends on 1)

The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R2 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

### Claim 4 (depends on 1)

The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the compounds represented by the Chemical Formula 1 is any one selected from the group consisting of the following:
1) 1-((3S,4R)-3-(5-chloro-2-(1-ethyl-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one,
2) 1-((3S,4R)-3-(5-chloro-2-(1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one,
3) 1-((3S,4R)-3-(5-chloro-2-(1-cyclopropyl-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one,
4) 1-((3S,4R)-3-(5-chloro-2-(isoxazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one,
5) 1-((3S,4R)-3-(5-chloro-2-(isothiazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one,
6) 4-((3S,4R)-1-acryloyl-4-fluoropiperidin-3-ylamino)-2-(1-ethyl-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
7) 4-((3S,4R)-1-acryloyl-4-fluoropiperidin-3-ylamino)-2-(1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
8) 4-((3S,4R)-1-acryloyl-4-fluoropiperidin-3-ylamino)-2-(1-cyclopropyl-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
9) 4-((3S,4R)-1-acryloyl-4-fluoropiperidin-3-ylamino)-2-(isoxazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
10) 1-((3S,4R)-3-(2-(1-ethyl-1H-pyrazol-4-ylamino)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one,
11) 1-((3S,4R)-4-fluoro-3-(2-(isoxazol-4-ylamino)-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)prop-2-en-1-one, and
12) 1-((3S,4S)-3-(5-chloro-2-(1-ethyl-1H-pyrazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-4-fluoropiperidin-1-yl)prop-2-en-1-one.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising the compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1)

A method for inhibiting the activity of JAK3 and/or BTK comprising administering to a subject in need thereof an effective amount of the compound according to claim 1 or a pharmaceutically acceptable salt thereof.