# US 12,215,102 B2 · Compositions and methods for making and using small molecules for tubulin-targeted therapy in the treatment of cancers and related conditions

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- Number: US 12,215,102 B2
- Document ID: US12215102B2
- Status: Granted
- Kind: B2
- Application number: 18/590,806
- Filed: 2024-02-28
- Published: 2024-10-03
- Granted: 2025-02-04
- Earliest claimed: 2023-02-28
- Assignees: Reglagene, Inc.
- Applicants: Reglagene, Inc.
- Inventors: Vijay Gokhale; Teri C. Suzuki
- Web page: https://patentgrep.com/patent/US12215102B2

## CPC

- C07D 417/14: containing three or more hetero rings
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 35/00: Antineoplastic agents
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 491/107: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D 498/08: Bridged systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

The novel compounds, compositions and methods disclosed herein are effective for treating a subject having or suspected of developing a health condition, for example, cancer (i.e. brain cancer or a cancer metastasizing to the brain). The method of treating cancer can include administering a pharmaceutical composition to a subject, the composition including at least one of the novel compounds disclosed herein, and optionally, one or more additional anti-cancer therapies. The compounds, compositions and methods can be further used for drug screening and other methods of detection and isolation.

## Claims

### Claim 1

A compound according to formula (I-D):
wherein R5 is selected from:
and
R6 is an aryl or a heteroaryl, wherein the aryl and the heteroaryl are each independently unsubstituted or are each independently substituted with one or more of an alkyl, alkenyl, alkynyl, alkoxyl, alkylsulfo, alkylamino, halogen, thiol, hydroxyl, nitro, cyano, cycloalkyl, heterocyclyl, heterocyclic alkyl, aryl, heteroaryl, cycloalkoxyl, heterocyclic alkoxyl, cycloalkylthio, or heterocyclic alkylthio.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R6 is one of the following:

### Claim 3

A composition comprising at least one compound according to formula (I-D):
and
one or more of the following: a tag, an inactive moiety or a targeting moiety linked to the compound;
wherein R5 is selected from:
and
R6 is an aryl or a heteroaryl, wherein the aryl and the heteroaryl are each independently unsubstituted or are each independently substituted with one or more of an alkyl, alkenyl alkynyl, alkoxyl, alkylsulfo, alkylamino, halogen, thiol, hydroxyl, nitro, cyano, cycloalkyl, heterocyclyl, heterocyclic alkyl, aryl, heteroaryl, cycloalkoxyl, heterocyclic alkoxyl cycloalkylthio, or heterocyclic alkylthio.

### Claim 4 (depends on 3)

The compound of claim 3, wherein the tag is a fluorescent tag, radioactive tag, biotin, or any combination thereof.

### Claim 5 (depends on 3)

The compound of claim 3, wherein the inactive moiety is an ester, carbamate, aminoacyl ester, or any combination thereof.

### Claim 6 (depends on 3)

The compound of claim 3, wherein the targeting moiety is an antibody, polyethylene glycol (PEG) conjugate, or long chain polymer, peptide sequence, or any combination thereof.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound is:

### Claim 8 (depends on 1)

A composition comprising at least one compound according to claim 1.

### Claim 9

A compound according to formula II-D:
wherein J is:
wherein L is:
and
wherein K is an aryl or a heteroaryl, wherein the aryl and the heteroaryl are each independently unsubstituted or are independently substituted with one or more groups selected from alkyl, alkenyl, alkynyl, alkoxyl, alkylsulfo, alkylamino, halogen, thiol, hydroxyl, nitro, cyano, cycloalkyl, heterocyclic alkyl, aryl, heterocyclyl, heteroaryl, cycloalkoxyl, heterocyclic alkoxyl, cycloalkylthio, and heterocyclic alkylthio.

### Claim 10 (depends on 9)

The compound of claim 9, wherein K is selected from the following:

### Claim 11 (depends on 9)

A composition comprising at least one compound according to claim 9.