# US 10,441,607 B1 · Multifunctional linker technology containing an N4 group

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,441,607 B1
- Document ID: US10441607B1
- Status: Granted
- Kind: B1
- Application number: 15/439,515
- Filed: 2017-02-22
- Granted: 2019-10-15
- Earliest claimed: 2016-02-22
- Assignees: Board of Regents, The University of Texas System
- Applicants: The Board of Regents of the University of Texas System
- Inventors: Ali Azhdarinia; Sukhen C. Ghosh; Nathaniel L. Wilganowski; Eva M. Sevick-Muraca
- Web page: https://patentgrep.com/patent/US10441607B1

## CPC

- A61K 33/02: Ammonia; Compounds thereof
- A61K 33/24: Heavy metals; Compounds thereof
- A61K 33/243: Platinum; Compounds thereof
- A61K 33/244: Lanthanides; Compounds thereof (medicinal preparations containing radioactive lanthanides for use in therapy or testing in vivo A61K51/00)
- A61K 38/16: Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof {(enzyme inhibitors A61K38/005)}
- A61K 39/385: Haptens or antigens, bound to carriers
- A61K 39/395: Antibodies (agglutinins A61K38/36 {; as drug carriers A61K47/50}); Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- A61K 47/64: Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent (peptidic linkers A61K47/65)
- A61K 47/6803: {Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates}
- A61K 47/6849: {the antibody targeting a receptor, a cell surface antigen or a cell surface determinant}
- A61K 49/0002: {General or multifunctional contrast agents, e.g. chelated agents}
- A61K 49/0021: {the fluorescent group being a small organic molecule}
- A61K 49/0032: {Methine dyes, e.g. cyanine dyes}
- A61K 49/0056: {Peptides, proteins, polyamino acids}
- A61K 49/0058: {Antibodies}
- A61K 51/083: {the peptide being octreotide or a somatostatin-receptor-binding peptide}
- A61K 51/088: {conjugates with carriers being peptides, polyamino acids or proteins (antibodies A61K51/10)}
- A61K 51/1027: {against receptors, cell-surface antigens or cell-surface determinants}
- A61K 51/1093: {conjugates with carriers being antibodies}
- C07K 16/28: against receptors, cell surface antigens or cell surface determinants
- A61K 2039/5152: {Tumor cells}
- 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)
- 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

In some aspects, the present disclosure provides compositions comprising an N4-based MMC ligand, a cell targeting group, and a fluorophore or a therapeutic compound comprising a formula: wherein the variables are as defined herein. In some embodiments, these compositions may be used in the imaging techniques or in the treatment of a disease or disorder such as cancer.

## Claims

### Claim 1

A compound of the formula:
wherein:
two of R1, R2, R3, and R4 are -A-COR5, wherein:
A is alkanediyl(C≤8) or substituted alkanediyl(C≤8); and
R5 is hydroxy, alkoxy(C≤8), or substituted alkoxy(C≤8);
one of R1, R2, R3, or R4 is a peptide group, wherein the peptide group comprises a conjugated antibody that comprises a light and heavy variable region;
one of R1, R2, R3, and R4 is a fluorophore group or
a chemotherapeutic group; and
M is a metal atom of any oxidation state or absent;
or a pharmaceutically acceptable salt thereof, wherein:
R5 is alkoxy(C≤8); or
R4 is a chemotherapeutic group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R5 is hydroxy.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R5 is alkoxy(C≤8).

### Claim 4 (depends on 1)

The compound of claim 1, wherein the peptide group further comprises a linker which joins the peptide to formula I.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R2 is the peptide group that comprises the conjugated antibody and R4 is a fluorophore group or chemotherapeutic group.

### Claim 6 (depends on 5)

The compound of claim 5, wherein the peptide group further comprises a linker which joins the antibody to formula I.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R4 is a chemotherapeutic group.

### Claim 8 (depends on 7)

The compound of claim 7, wherein the chemotherapeutic group further comprises a linker which joins the chemotherapeutic compound to formula I.

### Claim 9 (depends on 7)

The compound of claim 7, wherein the chemotherapeutic group is further defined by the formula:

### Claim 10 (depends on 1)

The compound of claim 1, wherein R4 is a fluorophore group.

### Claim 11 (depends on 10)

The compound of claim 10, wherein the fluorophore group is further defined by the formula:

### Claim 12 (depends on 10)

The compound of claim 10, wherein the fluorophore group further comprises a linker which joins the fluorophore to formula I.

### Claim 13 (depends on 12)

The compound of claim 12, wherein the fluorophore is further defined by the formula:

### Claim 14 (depends on 1)

The compound of claim 1, wherein M is a transition metal atom.

### Claim 15 (depends on 1)

The compound of claim 1, further defined as:
wherein:
and
Rb is the peptide group that comprises the conjugated antibody;
or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 1)

A pharmaceutical composition comprising:
(a) the compound of claim 1; and
(b) a pharmaceutically acceptable carrier.

### Claim 17 (depends on 1)

A method of delivering a compound or composition of claim 1 to a cell comprising contacting the cell with the compound or composition.