# US 8,785,661 B2 · Oligome-containing pyrrolidine compounds

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- Number: US 8,785,661 B2
- Document ID: US8785661B2
- Status: Granted
- Kind: B2
- Application number: 13/319,924
- Filed: 2010-05-13
- Published: 2012-04-26
- Granted: 2014-07-22
- Earliest claimed: 2009-05-13
- Assignees: Nektar Therapeutics
- Applicants: Jennifer Riggs-Sauthier
- Inventors: Jennifer Riggs-Sauthier
- Web page: https://patentgrep.com/patent/US8785661B2

## CPC

- A61K 31/4015: having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
- A61K 31/765: Polymers containing oxygen
- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- C07D 207/267: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
- C07D 207/27: with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to (among other things) oligomer-containing pyrrolidine compounds. A compound of the invention, when administered by any of a number of administration routes, exhibits one or more advantages over corresponding compounds lacking the oligomer.

## Claims

### Claim 1

A compound comprising a pyrrolidine residue covalently attached via a stable linkage to a water-soluble, non-peptidic oligomer, wherein the compound is encompassed within the formula:
wherein:
each L is independently selected from the group consisting of hydrogen, hydroxyl, a C1-6 alkyl radical, a C2-6 alkenyl radical, and a C2-6 alkynyl radical;
p is a whole number from 1 to 6;
Y is selected from the group consisting of hydrogen, a C1-6 alkyl radical, a C2-6 alkenyl radical, and a C2-6 alkynyl radical;
R2 is selected from the group consisting of hydrogen, an alkyl radical, an alkenyl radical, an alkynyl radical, a cycloalkyl radical, and an aryl radical;
X is a spacer moiety; and
POLY is a water-soluble, non-peptidic oligomer having a molecular weight of below about 1500 Daltons.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the pyrrolidine residue is a residue of a pyrrolidine moiety encompassed within the formula:
wherein:
each L is independently selected from the group consisting of hydrogen, hydroxyl, a C1-6 alkyl radical, a C2-6 alkenyl radical, and a C2-6 alkynyl radical;
p is a whole number from 1 to 6;
Y is selected from the group consisting of hydrogen, a C1-6 alkyl radical, a C2-6 alkenyl radical, and a C2-6 alkynyl radical; and
either R1 and R2 are each independently selected from the group consisting of hydrogen, a C1-6 alkyl radical, a C2-6 alkenyl radical, a C2-6 alkynyl radical, a C3-6 cycloalkyl radical, and an aryl radical,
or R1 and R2, together with the nitrogen atom to which they are attached, form a heterocyclic radical.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the pyrrolidine residue is a residue of a pyrrolidine moiety selected from the group consisting of levetiracetam, piracetam, brivaracetam, nefiracetam and oxiracetam.

### Claim 4 (depends on 3)

The compound of claim 3, wherein the pyrrolidine residue is a residue of a pyrrolidine moiety selected from the group consisting of levetiracetam, piracetam, brivaracetam and nefiracetam.

### Claim 5 (depends on 4)

The compound of claim 4, wherein the pyrrolidine residue is a residue of levetiracetam.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the water-soluble, non-peptidic oligomer is a poly(alkylene oxide).

### Claim 7 (depends on 6)

The compound of claim 6, wherein the poly(alkylene oxide) is a poly(ethylene oxide).

### Claim 8 (depends on 1)

The compound of claim 1, wherein the water-soluble, non-peptidic oligomer has from about 1 to about 30 monomers.

### Claim 9 (depends on 8)

The compound of claim 8, wherein the water-soluble, non-peptidic oligomer has from about 1 to about 10 monomers.

### Claim 10 (depends on 7)

The compound of claim 7, wherein the poly(alkylene oxide) includes an alkoxy or hydroxy end-capping moiety.

### Claim 11 (depends on 1)

The compound of claim 1, wherein a single water-soluble, non-peptidic oligomer is covalently attached to the pyrrolidine residue.

### Claim 12 (depends on 1)

The compound of claim 1, wherein two water-soluble, non-peptidic oligomers are covalently attached to the pyrrolidine residue.