# US 11,299,489 B1 · Thiazole compounds as protein kinase inhibitors

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- Number: US 11,299,489 B1
- Document ID: US11299489B1
- Status: Granted
- Kind: B1
- Application number: 16/952,600
- Filed: 2020-11-19
- Granted: 2022-04-12
- Earliest claimed: 2020-11-19
- Assignees: National Health Research Institutes; Taivex Therapeutics Corporation
- Applicants: National Health Research Institutes; Taivex Therapeutics Corporation
- Inventors: Weir-Torn Jiaang; Yu-Sheng Chao
- Web page: https://patentgrep.com/patent/US11299489B1

## CPC

- C07D 417/14: containing three or more hetero rings
- A61P 35/02: specific for leukemia
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Thiazole compounds of Formula (I) shown below and pharmaceutical compositions containing one of such compounds: wherein R1 and R2 are defined in the specification. Also disclosed are methods of inhibiting a tyrosine kinase and treating cancer associated with a tyrosine kinase with one of the thiazole compounds.

## Claims

### Claim 1

A compound of formula (I) below or a pharmaceutically acceptable salt thereof:
wherein,
R1 is C1-6 alkyl; and
R2 is heteroaryl.

### Claim 2 (depends on 1)

The compound or salt of claim 1, wherein R1 is methyl.

### Claim 3 (depends on 1)

The compound or salt of claim 1, wherein R2 is 6-membered heteroaryl.

### Claim 4 (depends on 3)

The compound or salt of claim 3, wherein R2 is pyridyl.

### Claim 5 (depends on 1)

The compound or salt of claim 1, wherein the compound is of formula (II):

### Claim 6 (depends on 5)

The compound or salt of claim 5, wherein R1 is methyl.

### Claim 7 (depends on 5)

The compound or salt of claim 5, wherein R2 is 6-membered heteroaryl.

### Claim 8 (depends on 7)

The compound or salt of claim 7, wherein R2 is pyridyl.

### Claim 9 (depends on 1)

The compound or salt of claim 1, which is

### Claim 10

A pharmaceutical composition, comprising:
a pharmaceutically acceptable carrier; and
a compound of formula (I) below or a pharmaceutically acceptable salt thereof:
wherein,
R1 is C1-6 alkyl; and
R2 is heteroaryl.

### Claim 11 (depends on 10)

The pharmaceutical composition of claim 10, wherein the compound is

### Claim 12

A method of inhibiting a tyrosine kinase, comprising contacting the tyrosine kinase with an effective amount of a compound of formula (I) below or a pharmaceutically acceptable salt thereof:
wherein,
R1 is C1-6 alkyl; and
R2 is heteroaryl.

### Claim 13 (depends on 12)

The method of claim 12, wherein the compound is

### Claim 14

A method of treating cancer associated with a tyrosine kinase, the method comprising administering to a subject in need thereof an effective amount of a compound of formula (I) below or a pharmaceutically acceptable salt thereof:
wherein,
R1 is C1-6 alkyl; and
R2 is heteroaryl.

### Claim 15 (depends on 14)

The method of claim 14, wherein the tyrosine kinase is FMS-like tyrosine kinase 3 (FLT3), FMS-like tyrosine kinase 4, vascular endothelial growth factor receptor (VEGFR), colony stimulating factor 1 receptor (CSF1R), platelet-derived growth factor receptor (PDGFR) A, PDGFR B, tyrosine-protein kinase Kit (c-KIT), c-Src (SRC), tyrosine-protein kinase Lyn (LYN) A, LYN B, rearranged during transfection tyrosine kinase (RET), lymphocyte-specific protein tyrosine kinase, Gardner-Rasheed feline sarcoma viral oncogene homolog, discoidin domain receptor 1, kinase insert domain receptor, B lymphocyte kinase, tyrosine-protein kinase Yes, Abelson murine leukemia viral oncogene homolog 1 (ABL1), tyrosine receptor kinase TRKA, TRKB, TRKC, ZAK/MLTK, IRAK4, RET V804L, RET Y791F, FLT3 D835Y, PDGFR A V561D, or ABL1 T315I.

### Claim 16 (depends on 15)

The method of claim 15, wherein the tyrosine kinase is FLT3 or c-KIT.

### Claim 17 (depends on 16)

The method of claim 16, wherein the cancer is acute myeloid leukemia, chloroma, chronic myelogenous leukemia, acute lymphoblastic leukemia, chronic lymphocytic leukemia, Hodgkin's disease, non-Hodgkin's lymphoma, B-cell lymphoma, multiple myeloma, Waldenstrom's macroglobulinemia, myelodysplastic syndrome, pancreatic cancer, bladder cancer, colorectal cancer, breast cancer, male genital tract cancer, renal cancer, hepatocellular cancer, lung cancer, ovarian cancer, cervical cancer, uterus cancer, gestational trophoblastic disease, gastric cancer, bile duct cancer, gallbladder cancer, small intestine cancer, esophageal cancer, oropharyngeal cancer, hypopharyngeal cancer, eye cancer, nerve cancer, head and neck cancer, melanoma, plasmacytoma, endocrine gland neoplasm, neuroendocrine cancer, brain tumor, bone cancer, or sarcoma.

### Claim 18 (depends on 17)

The method of claim 17, wherein the cancer is acute myeloid leukemia.

### Claim 19 (depends on 14)

The method of claim 14, wherein the compound is

### Claim 20 (depends on 18)

The method of claim 18, wherein the compound is