# US 11,897,901 B1 · 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile as anticancer compound

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- Number: US 11,897,901 B1
- Document ID: US11897901B1
- Status: Granted
- Kind: B1
- Application number: 18/239,258
- Filed: 2023-08-29
- Granted: 2024-02-13
- Earliest claimed: 2023-08-29
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Amer A. Amer; Antar Ahmed Abdelhamid Ahmed
- Web page: https://patentgrep.com/patent/US11897901B1

## CPC

- C07D 513/14: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- C07D 513/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile, its synthesis, and its use as an anticancer agent.

## Claims

### Claim 1

A 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound having the formula I:

### Claim 2 (depends on 1)

The 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound of claim 1, wherein the compound is obtained as crystals.

### Claim 3 (depends on 1)

The 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound of claim 1, having a melting point of about 234° C. to about 236° C.

### Claim 4 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method of making the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound of claim 1, the method comprising:
mixing equimolar amounts of 4-methoxybenzaldehyde and malonitrile in isopropyl alcohol in a presence of NH4OH as a basic catalyst for at least about 2 hours followed by adding thizolidine-2,4-dione to obtain a reaction mixture;
refluxing the reaction mixture for at least about 2 hours to obtain a precipitate; and
obtaining the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound.

### Claim 6 (depends on 5)

The method of making the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound of claim 5, wherein the precipitate is collected by filtration, washed several times with ethanol, dried, and recrystallized from the ethanol to obtain the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound.

### Claim 7 (depends on 5)

The method of making the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound of claim 5, wherein the 6-amino-8,9-di(4-methoxyphenyl)-2-oxo-3,9-dihydro-2H-[1,3]thiazolo[5′,4′:5,6]pyrano[2,3-b]pyridine-7-carbonitrile compound is obtained in an about 87% yield.