# US 11,999,755 B1 · Effective anticancer drug candidate of dinuclear palladium (II) bis-dihydrozone malonyl complex

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- Number: US 11,999,755 B1
- Document ID: US11999755B1
- Status: Granted
- Kind: B1
- Application number: 18/405,787
- Filed: 2024-01-05
- Granted: 2024-06-04
- Earliest claimed: 2024-01-05
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mohamed Shaker Sayed Adam; Amel Musa Taha; Alhanoof Saad Ibrahim Alghanim
- Web page: https://patentgrep.com/patent/US11999755B1

## CPC

- C07F 15/0066: {without a metal-carbon linkage}
- A61K 31/28: Compounds containing heavy metals
- A61P 35/00: Antineoplastic agents
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A dinuclear palladium (II) bis-dihydrozone malonyl complex, its synthesis, and its use as anti-cancer agents.

## Claims

### Claim 1

A palladium (II) bis-malonyl dihydrazone chelate complex having the formula:

### Claim 2 (depends on 1)

The palladium (II) bis-malonyl dihydrazone chelate complex of claim 1, wherein the palladium (II) bis-malonyl dihydrazone chelate complex is pale brown.

### Claim 3 (depends on 1)

The palladium (II) bis-malonyl dihydrazone chelate complex of claim 1, wherein the palladium (II) bis-malonyl dihydrazone chelate complex has a melting point of 300° C.

### Claim 4 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the palladium (II) bis-malonyl dihydrazone chelate complex of claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method of treating cancer selected from the group consisting of hepatocellular carcinoma, colon carcinoma, and breast adenocarcinoma in a patient comprising administering to a subject in need thereof a therapeutically effective amount of the palladium (II) bis-malonyl dihydrazone chelate complex of claim 1.

### Claim 6 (depends on 1)

A method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 1, the method comprising:
combining malonyl dihydrazone-isatin ligand with ethanol and palladium chloride to form a complexation reaction mixture;
stirring the complexation reaction mixture;
heating the complexation reaction mixture;
removing the ethanol from the complexation reaction mixture;
purifying a crude solid through recrystallization to obtain a pure complex;
washing the pure complex; and
obtaining the palladium (II) bis-malonyl dihydrazone chelate complex.

### Claim 7 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the H2L is a Schiff base hydrazone ligand (HL).

### Claim 8 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the stirring is magnetic stirring.

### Claim 9 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex, of claim 6, wherein the complexation reaction mixture is heated to about 80° C.

### Claim 10 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex, of claim 6, wherein the complexation reaction mixture is heated for about 3.5 hours.

### Claim 11 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the removing the ethanol from the complexation reaction mixture is through evacuation.

### Claim 12 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the crude solid is purified using ethanol.

### Claim 13 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the pure complex is washed with n-hexane.

### Claim 14 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein H2L and palladium chloride are added in a 1:2 molar ratio.

### Claim 15 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the palladium (II) bis-malonyl dihydrazone chelate complex is obtained in about a 68% yield.

### Claim 16 (depends on 6)

The method of making the palladium (II) bis-malonyl dihydrazone chelate complex of claim 6, wherein the palladium (II) bis-malonyl dihydrazone chelate complex has a melting point of 300° C.