# US 2019/0375758 A1 · Thiochromene type compound and use thereof

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- Number: US 2019/0375758 A1
- Document ID: US20190375758A1
- Status: Published application
- Kind: A1
- Application number: 15/577,239
- Filed: 2015-06-18
- Published: 2019-12-12
- Earliest claimed: 2015-05-27
- Assignees: Diatech Korea Co., Ltd.; Sogang University Research Foundation
- Applicants: Diatech Korea Co., Ltd.; Sogang University Research Foundation
- Inventors: Bong-Jin MOON; Han-Bin OH; Na-Na KANG; Ae-Ran JEON; Kye-Shin PARK; Je-Hyun BAEK
- Web page: https://patentgrep.com/patent/US20190375758A1

## CPC

- C07D 335/10: Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D 495/04: Ortho-condensed systems
- C07D 335/16: Oxygen atoms, e.g. thioxanthones
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- G01N 33/6851: {Methods of protein analysis involving laser desorption ionisation mass spectrometry}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

This invention relates to a photocleavable mass tag and the use thereof, and particularly to a thiochromene-type compound useful for MALDI-TOF (Matrix-Assisted Laser Desorption/Ionization Time-Of-Flight) mass spectrometry or matrix-less LDI-TOF (Laser Desorption/Ionization Time-Of-Flight) mass spectrometry and the use thereof.

## Claims

### Claim 1

A compound represented by Formula I below:
In Formula I, R1 is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group,
R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine, and
Ar is benzene or a heteroaromatic ring selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine).

### Claim 2

A compound represented by Formula II below:
in Formula II, R1 is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group, and
R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine).

### Claim 3

A compound represented by Formula III below:
in Formula III, R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring,
C(═O)R4 is N-hydroxysuccinimidyl, N-hydroxy sulfosuccinimidyl, pentafluorophenyloxy, 4-sulfo-2,3,5,6-tetrafluorophenyloxy, nitrophenyloxy, 2,4,5-trichlorophenyloxy, phthalimidoyloxy, N-hydroxy-5-norbomen-endo-2,3-dicarboimidyloxy, or maleimide, and
n is an integer of 1-12,
the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine).

### Claim 4

A compound represented by Formula IV below:
in Formula IV, R1 is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group, and
R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine).

### Claim 5

A compound represented by Formula V below:
in Formula V, A is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group,
R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine, and
Ar is benzene or a heteroaromatic ring selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine).

### Claim 6 (depends on 1, 2, 3, 4, 5)

The compound of any one of claims 1 to 5, which is used for MALDI-TOF (Matrix-Assisted Laser Desorption/Ionization Time-Of-Flight) mass spectrometry or matrix-less LDI-TOF (Laser Desorption/Ionization Time-Of-Flight) mass spectrometry.

### Claim 7

A conjugate compound of a biomaterial and a compound represented by Formula Ia below:
in Formula Ia, A is a C1-12 alkyl group, a C6-60 aryl group, or a C2-60 heteroaryl group containing at least one heteroatom selected from among N, S and O, having a reactive group at a terminal thereof, the reactive group being any one of a N-hydroxysuccinimide ester group, a N-hydroxysulfosuccinimide ester group, a pentafluorophenyl ester group, a 4-sulfo-2,3,5,6-tetrafluorophenyl ester group, a nitrophenyl ester group, a 2,4,5-trichlorophenyl ester group, a phthalimido ester group, a N-hydroxy-5-norbornen-endo-2,3-dicarboimide ester group, and a maleimide group,
R2 and R3 are independently hydrogen, a C1-12 alkyl, a C6-60 aryl, a C1-12 alkoxy, a C1-12 alkylamino, a C1-12 alkylthio or a fused ring, the fused ring being any one selected from among pyrrole, thiophene, indole, furan, imidazole, triazole, diazole, and pyrimidine, and
Ar is benzene or a heteroaromatic ring selected from among pyrrole, thiophene, indole, imidazole, triazole, and pyrimidine)
wherein the biomaterial is an antigen, an antibody, a biomarker, a peptide, a nucleic acid, or a glycan.

### Claim 8 (depends on 7)

The conjugate compound of claim 7, wherein the antibody is a monoclonal antibody.

### Claim 9 (depends on 7, 8)

The conjugate compound of claim 7 or 8, which is used for MALDI-TOF (Matrix-Assisted Laser Desorption/Ionization Time-Of-Flight) mass spectrometry or matrix-less LDI-TOF (Laser Desorption/Ionization Time-Of-Flight) mass spectrometry.