# US 11,306,103 B2 · Thieno[3,2-b]pyridine-5(4H)-one derivative compound, preparation method thereof and use thereof

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- Number: US 11,306,103 B2
- Document ID: US11306103B2
- Status: Granted
- Kind: B2
- Application number: 16/768,251
- Filed: 2017-12-27
- Published: 2021-06-10
- Granted: 2022-04-19
- Earliest claimed: 2017-11-30
- Assignees: Korea Institute of Ocean Science & Technology
- Applicants: Korea Institute of Ocean Science & Technology
- Inventors: Jong Seok Lee; Dan Bi Sung; Bo Hyun Mun; Hyi Seung Lee; Yeon Ju Lee; Ji Hoon Lee; Hee Jae Shin; Sol Park
- Web page: https://patentgrep.com/patent/US11306103B2

## CPC

- C07D 495/04: 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
- C09K 11/06: containing organic luminescent materials
- G01N 31/221: {for investigating pH value}
- G01N 33/533: with fluorescent label
- G01N 33/582: {with fluorescent label}
- G01N 33/84: involving inorganic compounds or pH
- C09K 2211/1018: Heterocyclic compounds
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

The present invention relates to a novel thieno[3,2-b]pyridine-5(4H)-one derivative compound, a preparation method thereof, and a use thereof. The novel thieno[3,2-b]pyridine-5(4H)-one derivative compound according to the present invention is synthesized via an aza-[3+3] cyclization addition reaction using BOP, wherein the compound is obtained by synthesizing a 4-arylthiophen-3-amine in which aryl groups such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4 are introduced via a synthesis process by a bromination reaction, a hydrolysis reaction, a decarboxylation reaction, and a Suzuki coupling reaction of methyl 3-aminothiophene carboxylate, and by synthesizing 4-arylthiophen-3-amine and mono-methyl fumarate via a formal aza-[3+3] cyclization addition reaction using BOP and conjugation. Accordingly, novel thieno[3,2-b]pyridine-5(4H)-one derivative compounds according to the present invention have fluorescence properties with a wide range of emission wavelengths and thus may be utilized in various industrial fields such as physics, chemistry, and biomedical research.

## Claims

### Claim 1

A compound selected from the group consisting of the compounds having the structural formulas 3 to 4, and 6 to 28, below:
structure
3
4
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28

### Claim 2

A method for preparing a compound of Chemical Formula 1 as illustrated in the following Reaction Scheme 1:
wherein,
R1 is H, Me, or Bn,
R2 is an aryl of C6-C10 that may be substituted or unsubstituted with one or more substituents overlappingly selected from the group consisting of a linear or branched alkyl of C1-C10, an amine, a 5- or 6-membered aromatic or non-aromatic heterocylic ring amine bearing one or two N atoms, F3CO—, an aryl of C6-C10, and an alkoxy of C1-C4; and
R3 is
H, Me, or Ph.

### Claim 3

A method for preparing a compound of Chemical Formula 1 as illustrated in the following Reaction Scheme 2:
wherein,
R1 is H, Me, or Bn,
R2 is an aryl of C6-C10 that may be substituted or unsubstituted with one or more substituents overlappingly selected from the group consisting of a linear or branched alkyl of C1-C10, an amine, a 5- or 6-membered aromatic or non-aromatic heterocylic ring amine bearing one or two N atoms, F3CO—, an aryl of C6-C10, and an alkoxy of C1-C4; and
R3 is
H, Me, or Ph.

### Claim 4

A method for preparing the compound of Chemical Formula 1 as illustrated in the following Reaction Scheme 3:
wherein,
R1 is H, Me, or Bn,
R2 is an aryl of C6-C10 that may be substituted or unsubstituted with one or more substituents overlappingly selected from the group consisting of a linear or branched alkyl of C1-C10, an amine, a 5- or 6-membered aromatic or non-aromatic heterocylic ring amine bearing one or two N atoms, F3CO—, an aryl of C6-C10, and an alkoxy of C1-C4; and
R3 is
H, Me, or Ph.

### Claim 5 (depends on 1)

A fluorescent composition, comprising the compound of claim 1, an enantiomer or diastereomer thereof, or an acid or base addition salt thereof as an active ingredient.

### Claim 6 (depends on 5)

A biomolecular labeling or analyzing kit comprising the fluorescent composition of claim 5.

### Claim 7 (depends on 1)

A pH sensing composition, comprising the compound of claim 1, an enantiomer or diastereomer thereof, or an acid or base addition salt thereof as a fluorescent dye.

### Claim 8 (depends on 7)

A pH sensor, comprising the pH sensing composition of claim 7.