# US 11,077,198 B2 · Pegylated carfilzomib compounds

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- Number: US 11,077,198 B2
- Document ID: US11077198B2
- Status: Granted
- Kind: B2
- Application number: 16/857,111
- Filed: 2020-04-23
- Published: 2020-12-03
- Granted: 2021-08-03
- Earliest claimed: 2016-05-24
- Assignees: Amgen Inc.
- Applicants: Amgen Inc.
- Inventors: Gary Luehr; Shabbir T. Anik; Ge Peng; Irina Dotsenko; Pasit Phiasivongsa; Dante Romanini
- Web page: https://patentgrep.com/patent/US11077198B2

## CPC

- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 38/07: Tetrapeptides
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 35/00: Antineoplastic agents
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C08G 65/33396: {having oxygen in addition to nitrogen}
- C08G 2230/00: Compositions for preparing biodegradable polymers
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention provides a method of treating multiple myeloma using polymeric pegylated carfilzomib compounds, and pharmaceutically acceptable salts thereof, of Formula I wherein R1, R2, linker, PEG, n and o are as defined herein.

## Claims

### Claim 1

A process of making a compound having the structure
the process comprising the step of
wherein X— is a counter ion salt selected from the group consisting of a chloride anion, a bisulfate anion, a sulfate anion, a nitrate anion, a phosphate anion, an alky-sulfonate anion or an aryl-sulfonate anion; R1 is C1-10alkyl or C3-7cycloalkyl; and PEG is a polyethylene glycol polymeric moiety having a molecular weight ranging from about 500 to about 20K.

### Claim 2 (depends on 1)

The process of claim 1, wherein R1 is C1-10alkyl.

### Claim 3 (depends on 2)

The process of claim 2, wherein R1 is methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl or heptyl.

### Claim 4 (depends on 2)

The process of claim 2, wherein R1 is methyl.

### Claim 5 (depends on 4)

The process of claim 4, wherein the PEG has a weight of 2K or 3K.

### Claim 6 (depends on 5)

The process of claim 5, wherein the PEG is linear PEG.

### Claim 7 (depends on 5)

The process of claim 5, wherein X— is an alky-sulfonate anion.

### Claim 8 (depends on 7)

The process of claim 7, wherein X— is mesylate.

### Claim 9 (depends on 4)

The process of claim 4, wherein X— is a chloride anion or an alky-sulfonate anion.

### Claim 10 (depends on 1)

The process of claim 1, wherein the PEG has a weight ranging from about 2K to about 20K.

### Claim 11 (depends on 10)

The process of claim 10, wherein the PEG is a linear PEG.

### Claim 12 (depends on 11)

The process of claim 11, wherein R1 is methyl or ethyl and X— is a chloride anion or an alky-sulfonate anion.

### Claim 13 (depends on 12)

The process of claim 12, wherein R1 is methyl.

### Claim 14 (depends on 10)

The process of claim 10, wherein the PEG has a weight of 2K, 3K, 5K or 20K.

### Claim 15 (depends on 10)

The process of claim 10, wherein the PEG has a weight of 2K, 3K, or 5K.

### Claim 16 (depends on 10)

The process of claim 10, wherein the PEG has a weight of 2K or 3K.

### Claim 17 (depends on 10)

The process of claim 10, wherein R1 is methyl.

### Claim 18 (depends on 16)

The process of claim 16, wherein X— is a chloride anion or an alky-sulfonate anion.

### Claim 19 (depends on 10)

The process of claim 10, wherein R1 is methyl or ethyl and X— is a chloride anion or an alky-sulfonate anion.

### Claim 20 (depends on 19)

The process of claim 19, wherein R1 is methyl.

### Claim 21 (depends on 1)

The process of claim 1, wherein X— is a chloride anion or an alky-sulfonate anion.

### Claim 22 (depends on 21)

The process of claim 21, wherein R1 is methyl and the PEG has a weight of 2K or 3K and the PEG is linear PEG.

### Claim 23 (depends on 21)

The process of claim 21, wherein the alky-sulfonate anion is mesylate.

### Claim 24 (depends on 21)

The process of claim 21, wherein the PEG has a weight ranging from about 2K to about 20K.

### Claim 25 (depends on 24)

The process of claim 24, wherein the PEG is linear PEG.