# US 10,479,807 B2 · Silylated pyrimidine prodrugs and methods of their use

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- Number: US 10,479,807 B2
- Document ID: US10479807B2
- Status: Granted
- Kind: B2
- Application number: 15/516,653
- Filed: 2015-10-08
- Published: 2017-10-26
- Granted: 2019-11-19
- Earliest claimed: 2014-10-08
- Assignees: Epigenetics Phrama LLC
- Applicants: Epigenetics Pharma LLC
- Inventors: Richard Daifuku; Dmitri S. Sergueev
- Web page: https://patentgrep.com/patent/US10479807B2

## CPC

- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- A61K 31/695: Silicon compounds
- A61P 35/02: specific for leukemia
- C07F 7/1872: {Preparation; Treatments not provided for in C07F7/20}
- C07H 19/06: Pyrimidine radicals
- C07H 19/12: Triazine radicals
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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
- 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

Silylated-pyrimidine prodrugs, compositions that include the silylated-pyrimidine prodrugs, methods for making the silylated-pyrimidine prodrugs and compositions, and methods for treating cancer using the silylated-pyrimidine prodrugs and compositions.

## Claims

### Claim 1

A compound having the formula:
wherein R1, R2, R7, and R8 are independently selected from hydrogen or Si(R4)(R5)(R6), wherein R4, R5, and R6 are independently selected from hydrogen or alkyl, provided that at least one of R1, R2, R7, or R8 is Si(R4)(R5)(R6).

### Claim 2 (depends on 1)

The compound of claim 1 having the formula:
wherein R1, R2, and R7 are independently selected from hydrogen or Si(R4)(R5)(R6), wherein R4, R5, and R6 are independently selected from hydrogen or alkyl, provided that at least one of R1, R2, or R7 is Si(R4)(R5)(R6).

### Claim 3 (depends on 1)

The compound of claim 1 having the formula:
wherein R1 and R2 are independently selected from hydrogen or Si(R4)(R5)(R6), wherein R4, R5, and R6 are independently selected from hydrogen or alkyl, provided that at least one of R1 or R2 is Si(R4)(R5)(R6).

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1 and R2 are Si(R4)(R5)(R6) and R4, R5, and R6 are methyl.

### Claim 5 (depends on 1)

A pharmaceutical composition, comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 6

A method for delivery of a compound to a tumor site by enhanced permeability and retention, comprising administering an effective amount of a compound having the formula:
wherein R1 and R2 are Si(CH3)3, to a tumor site in the subject in need thereof.

### Claim 7

A method for treating a solid tumor carcinoma, comprising administering an effective amount of a compound having the formula:
wherein R1 and R2 are Si(CH3)3, to a subject in need thereof.

### Claim 8 (depends on 7)

The method of claim 7, wherein the solid tumor carcinoma is selected from the group consisting of breast, non-small cell lung, and colon carcinomas.

### Claim 9 (depends on 6)

The method of claim 6, wherein the subject is a human.

### Claim 10 (depends on 7)

The method of claim 7, wherein the subject is human.

### Claim 11 (depends on 4)

The compound of claim 4, having the formula:
wherein R1 and R2 are Si(CH3)3.