# US 11,298,369 B2 · Composition and uses thereof

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- Number: US 11,298,369 B2
- Document ID: US11298369B2
- Status: Granted
- Kind: B2
- Application number: 16/442,061
- Filed: 2019-06-14
- Published: 2019-10-17
- Granted: 2022-04-12
- Earliest claimed: 2016-12-15
- Assignees: Progen PG500 Series Pty Ltd
- Applicants: Progen PG500 Series Pty Ltd
- Inventors: Keith Dredge
- Web page: https://patentgrep.com/patent/US11298369B2

## CPC

- A61K 31/704: attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin {(digitoxin A61K31/7048)}
- A61K 39/3955: {against proteinaceous materials, e.g. enzymes, hormones, lymphokines}
- A61K 39/39558: {against tumor tissues, cells, antigens}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- C07K 16/2818: {against CD28 or CD152}
- A61K 2039/505: {comprising antibodies}
- C07K 2317/76: Antagonist effect on antigen, e.g. neutralization or inhibition of binding
- 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
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

The present invention relates, inter alia, to methods for the prevention or treatment of cancer, and to compositions, combinations and kits for the treatment or prevention of cancer. In one embodiment, the invention provides a method of treating or preventing cancer, comprising administering to a patient in need thereof an immune checkpoint modulator together with a compound of Formula (I): wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation; and wherein at least 70% of the X groups is SO3M.

## Claims

### Claim 1

A method of treating or preventing cancer, comprising administering to a patient in need thereof an immune checkpoint inhibitor together with a compound of Formula (I):
wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation;
wherein at least 70% of the X groups is SO3M; and
wherein the immune checkpoint inhibitor is a PD-1 inhibitor or a PD-L1 inhibitor.

### Claim 2 (depends on 1)

The method of claim 1, wherein at least 90% of the X groups is SO3M.

### Claim 3 (depends on 1)

The method of claim 1, wherein the compound of Formula (I) is a compound of Formula (VI):

### Claim 4 (depends on 1)

The method of claim 1, wherein the immune checkpoint inhibitor targets one or more of a T cell, a Natural Killer (NK) cell, a Natural Killer T cell (NKT), a Gamma Delta T cell, an invariant T cell, or an invariant Natural Killer T cell (NKT).

### Claim 5 (depends on 1)

The method of claim 1, wherein the immune checkpoint inhibitor is a T cell immune checkpoint inhibitor.

### Claim 6

A method of treating or preventing cancer, comprising administering to a patient in need thereof Nivolumab together with a compound of Formula (I):
wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation; and
wherein at least 70% of the X groups is SO3M.

### Claim 7 (depends on 1)

The method of claim 1, wherein the cancer is a solid tumour.

### Claim 8 (depends on 3)

The method of claim 3, wherein the method is a method of treating cancer.

### Claim 9

A pharmaceutical composition or combination comprising a compound of Formula (I) and an immune checkpoint inhibitor, wherein the compound of Formula (I) is:
wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation;
wherein at least 70% of the X groups is SO3M; and
wherein the immune checkpoint inhibitor is a PD-1 inhibitor or a PD-L1 inhibitor.

### Claim 10

A pharmaceutical composition or combination, comprising a compound of Formula (I) and Nivolumab, wherein the compound of Formula (I) is:
wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation; and
wherein at least 70% of the X groups is SO3M.

### Claim 11

A kit comprising a compound of Formula (I) and an immune checkpoint inhibitor, wherein the compound of Formula (I) is:
wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation;
wherein at least 70% of the X groups is SO3M; and
wherein the immune checkpoint inhibitor is a PD-1 inhibitor or a PD-L1 inhibitor.

### Claim 12 (depends on 9)

The pharmaceutical composition or combination of claim 9, wherein at least 90% of the X groups is SO3M.

### Claim 13 (depends on 9)

The pharmaceutical composition or combination of claim 9, wherein the compound of Formula (I) is a compound of Formula (VI):

### Claim 14 (depends on 11)

The kit of claim 11, wherein at least 90% of the X groups is SO3M.

### Claim 15 (depends on 11)

The kit of claim 11, wherein the compound of Formula (I) is a compound of Formula (VI):

### Claim 16

A kit, comprising a compound of Formula (I) and Nivolumab, wherein the compound of Formula (I) is:
wherein X is SO3M or H, wherein M is any pharmaceutically acceptable cation; and
wherein at least 70% of the X groups is SO3M.

### Claim 17 (depends on 1)

The method of claim 1, wherein the immune checkpoint inhibitor is a PD-1 inhibitor.

### Claim 18 (depends on 9)

The pharmaceutical composition or combination of claim 9, wherein the immune checkpoint inhibitor is a PD-1 inhibitor.

### Claim 19 (depends on 11)

The kit of claim 11, wherein the immune checkpoint inhibitor is a PD-1 inhibitor.