# US 12,599,674 B2 · Conjugates, their compositions, and their related methods

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- Number: US 12,599,674 B2
- Document ID: US12599674B2
- Status: Granted
- Kind: B2
- Application number: 19/247,100
- Filed: 2025-06-24
- Published: 2025-10-16
- Granted: 2026-04-14
- Earliest claimed: 2021-12-15
- Assignees: The Administrators of the Tulane Educational Fund
- Applicants: The Administrators of the Tulane Educational Fund
- Inventors: Joseph A. Fuselier; David H. Coy
- Web page: https://patentgrep.com/patent/US12599674B2

## CPC

- A61K 47/643: {Albumins, e.g. HSA, BSA, ovalbumin or a Keyhole Limpet Hemocyanin [KHL]}
- A61K 9/19: lyophilised {, i.e. freeze-dried, solutions or dispersions (lyophilised products with subsequent particle size reduction A61K9/14; granules or pellets made by lyphilisation A61K9/1682; solid oral dosage forms made by lyophilisation A61K9/2095; lyophilisation additives A61K47/00)}
- A61P 35/00: Antineoplastic agents
- 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

Some embodiments of the invention include inventive compounds (e.g., compounds of Formula (I)). Other embodiments include compositions (e.g. pharmaceutical compositions) comprising the inventive compound. Still other embodiments of the invention include compositions for treating, for example, certain diseases using the inventive compounds. Some embodiments include methods of using the inventive compound (e.g., in compositions or in pharmaceutical compositions) for administering and treating. Further embodiments include methods for making the inventive compound. Additional embodiments of the invention are also discussed herein.

## Claims

### Claim 1

A compound of
wherein HSA is human serum albumin.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1.

### Claim 3 (depends on 2)

The pharmaceutical composition of claim 2, wherein the pharmaceutical composition comprises (a) the compound and (b) sucrose, mannitol, or both.

### Claim 4 (depends on 2)

The pharmaceutical composition of claim 2, wherein the pharmaceutical composition comprises a lyophilized composition comprising (a) the compound and (b) sucrose, mannitol, or both.

### Claim 5 (depends on 2)

The pharmaceutical composition of claim 2, wherein the pharmaceutical composition comprises the compound and sucrose.

### Claim 6 (depends on 2)

The pharmaceutical composition of claim 2, wherein the pharmaceutical composition comprises a lyophilized composition comprising the compound and sucrose.

### Claim 7 (depends on 2)

A method for treating a human for a disease, comprising an administration of the pharmaceutical composition of claim 2, wherein the disease is breast cancer, non-small cell lung cancer, pancreatic cancer, pancreatic ductal adenocarcinoma, ovarian cancer, glioblastoma multiforme, hepatocellular carcinoma, head and neck squamous cell carcinoma, gastric cancer, melanoma, lymphoma, or non-Hodgkin's lymphoma.

### Claim 8 (depends on 7)

The method of claim 7, wherein the disease is breast cancer, non-small cell lung cancer, lymphoma, gastric cancer, or ovarian cancer.

### Claim 9 (depends on 7)

The method of claim 7, wherein the disease is lymphoma or gastric cancer.

### Claim 10 (depends on 7)

The method of claim 7, wherein the disease is lymphoma.

### Claim 11 (depends on 2)

A method for treating a human for a lymphoma, comprising an administration of the pharmaceutical composition of claim 2, wherein the administration comprises a parenteral administration.

### Claim 12

A compound selected from the group consisting of:
wherein BSA is bovine serum albumin, CSA is canine serum albumin, FSA is feline serum albumin, and ESA is equine serum albumin.

### Claim 13 (depends on 12)

A pharmaceutical composition comprising the compound of claim 12.

### Claim 14 (depends on 13)

The pharmaceutical composition of claim 13, wherein the pharmaceutical composition comprises (a) the compound and sucrose or (b) a lyophilized composition comprising the compound and sucrose.

### Claim 15 (depends on 13)

The pharmaceutical composition of claim 13, wherein the pharmaceutical composition comprises (a) the compound, sucrose, and mannitol or (b) a lyophilized composition comprising the compound, sucrose, and mannitol.

### Claim 16 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein the animal is bovine, canine, feline, or equine and wherein the disease is lymphoma, gastric cancer, carcinomas, sarcomas, squamous cell carcinoma, melanoma, or cancerous tumors.

### Claim 17 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein
the animal is canine,
the compound is
and
the disease is lymphoma, gastric cancer, carcinomas, sarcomas, squamous cell carcinoma, melanoma, or cancerous tumors.

### Claim 18 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein
the animal is canine,
the compound is
and
the disease is lymphoma, gastric cancer, or melanoma.

### Claim 19 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein
the animal is feline,
the compound is
and
the disease is lymphoma, gastric cancer, carcinomas, sarcomas, squamous cell carcinoma, melanoma, or cancerous tumors.

### Claim 20 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein
the animal is feline,
the compound is
and
the disease is lymphoma or gastric cancer.

### Claim 21 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein
the animal is equine,
the compound is
and
the disease is lymphoma, gastric cancer, carcinomas, sarcomas, squamous cell carcinoma, melanoma, or cancerous tumors.

### Claim 22 (depends on 13)

A method for treating an animal for a disease, comprising an administration of the pharmaceutical composition of claim 13, wherein
the animal is equine,
the compound is, and
the disease is lymphoma, gastric cancer, or melanoma.

### Claim 23

A method for preparing a lyophilized composition comprising one or more of compounds I-1 to I-10, comprising
(a) providing one or more of compounds I-1 to I-10;
(b) contacting the one or more of compounds I-1 to I-10 of (a) with sucrose, mannitol, or both, to provide a mixture;
(c) freezing the mixture of (b); and
(d) removing water to provide a lyophilized composition comprising one or more of compounds I-1 to I-10,
wherein compounds I-1 to I-10 are:
where the Human Serum Albumin (HSA) is attached via its cys-34 thiol (I-1),
where the Bovine Serum Albumin (BSA) is attached via its cys-34 thiol (I-2),
where the Canine Serum Albumin (CSA) is attached via its cys-34 thiol (I-3),
where the Feline Serum Albumin (FSA) is attached via its cys-34 thiol (I-4),
where the Equine Serum Albumin (ESA) is attached via its cys-34 thiol (I-5),
where the Human Serum Albumin (HSA) is attached via its cys-34 thiol (I-6),
where the Bovine Serum Albumin (BSA) is attached via its cys-34 thiol (I-7),
where the Canine Serum Albumin (CSA) is attached via its cys-34 thiol (I-8),