# US 11,306,111 B2 · Organophosphate derivatives

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

- Number: US 11,306,111 B2
- Document ID: US11306111B2
- Status: Granted
- Kind: B2
- Application number: 16/635,469
- Filed: 2018-07-30
- Published: 2020-11-26
- Granted: 2022-04-19
- Earliest claimed: 2017-07-31
- Assignees: January Therapeutics, Inc.
- Applicants: January Therapeutics, Inc.
- Inventors: Raj Raheja; Robin M. Jackman
- Web page: https://patentgrep.com/patent/US11306111B2

## CPC

- C07F 9/65586: {at least one of the hetero rings does not contain nitrogen as ring hetero atom}
- A61P 35/00: Antineoplastic agents
- C07F 9/65742: {non-condensed with carbocyclic rings or heterocyclic rings or ring systems}
- C07F 9/65744: {condensed with carbocyclic or heterocyclic rings or ring systems}
- C07H 19/10: with the saccharide radical esterified by phosphoric or polyphosphoric acids
- C07H 19/11: containing cyclic phosphate
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Provided herein are organophosphates and pharmaceutical compositions comprising said compounds.

## Claims

### Claim 1

A compound having the structure of Formula (II):
wherein:
R3 is H, —C(O)R9, or —C(O)OR9;
R4 is H;
R9 is C1-8alkyl;
R11 is C6-22alkyl, C3-22alkenyl, C3-22alkynyl, C3-22haloalkyl, —C1-4alkyl-OC(O)C1-8alkyl, C6-10aryl, —C1-8alkyl-C6-10aryl, C2-9heteroaryl, or —C1-8alkyl-C2-9heteroaryl, wherein C6-10aryl, —C1-8alkyl-C6-10aryl, C2-9heteroaryl, or —C1-8alkyl-C2-9heteroaryl are optionally substituted with 1, 2, 3, or 4 R12;
each R12 is independently selected from halogen, C1-8alkyl, C1-8haloalkyl, C1-8alkoxy, and —C(O)R13; and
each R13 is independently selected from C1-12alkyl;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R11 is C6-22alkyl.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R11 is C16-22alkyl.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R11 is —C1-4alkyl-OC(O)C1-8alkyl.

### Claim 5 (depends on 4)

The compound of claim 4, or a pharmaceutically acceptable salt thereof, wherein R11 is —C1-2 alkyl-OC(O)C1-6alkyl.

### Claim 6 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt thereof, wherein R11 is —CH2—OC(O)C(CH3)3.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R11 is phenyl optionally substituted with 1, 2, or 3 R12.

### Claim 8 (depends on 7)

The compound of claim 7, or a pharmaceutically acceptable salt thereof, wherein R11 is phenyl optionally substituted with 1, 2, or 3 R12, and each R12 is independently selected from C1-8alkyl, C1-8alkoxy, and —C(O)R13.

### Claim 9 (depends on 8)

The compound of claim 8, or a pharmaceutically acceptable salt thereof, wherein R11 is phenyl optionally substituted with 1 or 2 R12, and each R12 is independently selected from C1-8alkyl and C1-8alkoxy.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R11 is —C1-8alkyl-C6-10aryl optionally substituted with 1, 2, 3, or 4 R12.

### Claim 11 (depends on 10)

The compound of claim 10, or a pharmaceutically acceptable salt thereof, wherein R11 is —CH2-phenyl optionally substituted with 1, 2, or 3 R12.

### Claim 12 (depends on 11)

The compound of claim 11, or a pharmaceutically acceptable salt thereof, wherein R11 is —CH2-phenyl optionally substituted with 1, 2, or 3 R12, and each R12 is independently selected from C1-8alkyl, C1-8alkoxy, and —C(O)R13.

### Claim 13 (depends on 12)

The compound of claim 12, or a pharmaceutically acceptable salt thereof, wherein R11 is —CH2-phenyl optionally substituted with 1 or 2 R12, and each R12 is independently selected from C1-8alkyl and C1-8alkoxy.

### Claim 14 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R3 is H.

### Claim 15 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R3 is —C(O)R9.

### Claim 16 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R3 is —C(O)OR9.

### Claim 17 (depends on 1)

The compound of claim 1 selected from:
or a pharmaceutically acceptable salt thereof.

### Claim 18 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable excipient.

### Claim 19 (depends on 1)

A method of treating cancer in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the cancer is selected from pancreatic cancer, bladder cancer, breast cancer, and non-small cell lung cancer.