# US 12,180,228 B2 · Compounds, conjugates, and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines and uses thereof

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- Number: US 12,180,228 B2
- Document ID: US12180228B2
- Status: Granted
- Kind: B2
- Application number: 18/146,294
- Filed: 2022-12-23
- Published: 2023-07-06
- Granted: 2024-12-31
- Earliest claimed: 2019-06-05
- Assignees: Massachusetts Institute of Technology
- Applicants: Massachusetts Institute of Technology
- Inventors: Mohammad Movassaghi; Chase Robert Olsson; Tony Z. Scott; Jaime Cheah; Joshua Nathaniel Payette
- Web page: https://patentgrep.com/patent/US12180228B2

## CPC

- C07D 513/22: in which the condensed system contains four or more hetero rings
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61P 35/00: Antineoplastic agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present disclosure provides, e.g., compounds, compositions, kits, methods of synthesis, and methods of use, involving epipolythiodiketopiperazines and polythiodiketopiperazines.

## Claims

### Claim 1

A compound having the structure of Formula (X):
or salt thereof, wherein
RX is unsubstituted alkyl, -Si(RS)3, -Sn(RS)3, substituted or unsubstituted benzyl, or MX;
RY is unsubstituted alkyl, -Si(RS)3, -Sn(RS)3, substituted or unsubstituted benzyl, hydrogen, or MY;
each RS is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
MX is a metal selected from the group consisting of sodium, potassium, lithium, rubidium, and cesium; and
MY is a metal selected from the group consisting of sodium, potassium, lithium, rubidium, and cesium.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is not sodium benzhydryl trithiocarbonate.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound is not sodium benzhydryl trithiocarbonate or sodium p-methoxybenzhydryl trithiocarbonate.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
wherein each RS′ is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein RX is MX.

### Claim 6 (depends on 5)

The compound of claim 5, wherein MX is sodium.

### Claim 7 (depends on 1)

The compound of claim 1, wherein RY is substituted or unsubstituted benzyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:

### Claim 9 (depends on 4)

The compound of claim 4, wherein the compound is of the formula:

### Claim 10 (depends on 4)

The compound of claim 4, wherein MX is sodium.

### Claim 11 (depends on 9)

The compound of claim 9, wherein MX is sodium.

### Claim 12 (depends on 4)

The compound of claim 4, wherein each RS′ is hydrogen.

### Claim 13 (depends on 10)

The compound of claim 10, wherein each RS′ is hydrogen.

### Claim 14 (depends on 9)

The compound of claim 9, wherein RS′ is hydrogen.

### Claim 15 (depends on 11)

The compound of claim 11, wherein RS′ is hydrogen.

### Claim 16 (depends on 4)

The compound of claim 4, wherein each RS′ is independently halogen, hydroxyl, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 17 (depends on 10)

The compound of claim 10, wherein each RS′ is independently halogen, hydroxyl, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 18 (depends on 9)

The compound of claim 9, wherein RS′ is halogen, hydroxyl, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 19 (depends on 11)

The compound of claim 11, wherein RS′ is halogen, hydroxyl, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 20 (depends on 9)

The compound of claim 9, wherein RS′ is substituted or unsubstituted C1-6 heteroalkyl.

### Claim 21 (depends on 11)

The compound of claim 11, wherein RS′ is substituted or unsubstituted C1-6 heteroalkyl.