# US 9,434,681 B2 · Macromolecules for treating atherosclerosis

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- Number: US 9,434,681 B2
- Document ID: US9434681B2
- Status: Granted
- Kind: B2
- Application number: 14/407,403
- Filed: 2013-06-17
- Published: 2015-06-25
- Granted: 2016-09-06
- Earliest claimed: 2012-06-15
- Assignees: Rutgers, The State University of New Jersey
- Applicants: Rutgers, the State University of New Jersey
- Inventors: Kathryn E. Uhrich; Dawanne E. Poree; Prabhas Moghe
- Web page: https://patentgrep.com/patent/US9434681B2

## CPC

- C07C 235/10: having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
- A61P 9/00: Drugs for disorders of the cardiovascular system
- C07C 69/708: Ethers
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention includes compounds of the formula I and formula II and salts thereof, as well as methods for using the compounds of formula I and formula II for treating atherosclerosis. The invention also includes compounds of formula III and (2l) and salts thereof, as well as methods of using the compounds of formula III and (2l) for treating atherosclerosis. The invention also includes methods of encapsulating molecules using the compounds of the invention.

## Claims

### Claim 1

A compound of formula II:
A-(CH(OC(═O)R3))n—W—W1—R2 II
wherein;
A is selected from carboxy, —SO3H and —PO3H;
n is independently 2, 3, 4, 5 or 6;
W is —C(═O)—, —C(═S)—, or is absent;
W1 is O, S or NH;
each R1 is independently a hydrophobic chain;
R2 is a polyether, wherein the polyether has the following structure:
R5—(R6—O—)a—R6—
wherein R5 is a 1 to 20 carbon straight-chain or branched alkyl group, —OH, —OR7, —NH2, —NHR7, —NHR7R8, —CO2H, —SO3H (sulfo), —CH2—OH, —CH2—OR7, —CH2—O—CH2—R7, —CH2—NH2, —CH2—NHR7, —CH2—NR7R8, —CH2CO2H, —CH2SO3H, or —O—C(═O)—CH2—CH2—C(═O)—O—;
R6 is a 1 to 10 carbon straight-chain or branched divalent alkylene group;
each R7 and R8 is independently a 1 to 6 carbon straight-chain or branched alkylene group; and
a is an integer from 2 to 150, inclusive; and
each R3 is independently (C1-C8)alkyl wherein each (C1-C8)alkyl is independently substituted with one or more —O(C═O)R1 groups;
or a salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein the compound of formula II is a compound of formula IIa:
wherein:
n is 2, 3, 4, 5 or 6;
each R1 is independently a hydrophobic chain;
R2 is a polyether, wherein the polyether has the following structure:
R5—(R6—O—)a—R6—
wherein R5 is a 1 to 20 carbon straight-chain or branched alkyl group, —OH, —OR7, —NH2, —NHR7, —NHR7R8, —CO2H, —SO3H (sulfo), —CH2—OH, —CH2—OR7, —CH2—O—CH2—R7, —CH2—NH2, —CH2—NHR7, —CH2—NR7R8, —CH2CO2H, —CH2SO3H, or —O—C(═O)—CH2—CH2—C(═O)—O—;
R6 is a 1 to 10 carbon straight-chain or branched divalent alkylene group;
each R7 and R8 is independently a 1 to 6 carbon straight-chain or branched alkylene group; and
a is an integer from 2 to 150, inclusive; and
each R3 is independently (C1-C8)alkyl wherein each (C1-C8)alkyl is independently substituted with one or more —O(C═O)R′ groups;
or a salt thereof.

### Claim 3 (depends on 1)

The compound of claim 1 wherein the polyether is a poly(alkylene oxide) having between about 2 and about 150 repeating units.

### Claim 4 (depends on 3)

The compound of claim 3, wherein each alkylene oxide unit comprises straight or branched (C2-C4) alkylene oxide.

### Claim 5 (depends on 1)

The compound of claim 1 wherein the polyether is a poly(ethylene oxide) having between about 2 and about 150 repeating units.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the polyether comprises an alkoxy-terminal group.

### Claim 7 (depends on 1)

The compound of claim 1 wherein the each R1 is independently (C1-C24)alkyl, (C2-C24)alkene or (C2-C24)alkyne.

### Claim 8 (depends on 1)

The compound of claim 1 wherein each R1 is independently a fatty acid, wherein the fatty acid is caprylic, capric, lauric, myristic, myristoleic, palmitic, palmitoleic, stearic, oleic, linoleic, arachidic, behenic, or erucic acid, or a mixture thereof.

### Claim 9 (depends on 1)

The compound of claim 1 wherein the each R1 is independently a (C6-C18)alkyl.

### Claim 10 (depends on 1)

The compound of claim 1 wherein n is independently 2 or 4.

### Claim 11 (depends on 2)

The compound of claim 2 wherein each R3 is independently a (C3-C6)alkyl.

### Claim 12 (depends on 1)

The compound of claim 1 selected from:
and salts thereof.

### Claim 13 (depends on 1)

A pharmaceutical composition comprising a compound of formula II as described in claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

### Claim 14 (depends on 1)

A method for preventing the uptake of LDL by a cell comprising contacting the cell with a compound of formula II as described in claim 1.

### Claim 15 (depends on 1)

A method for inhibiting atherosclerosis or atherosclerotic development in a mammal, comprising administering an anti-atherosclerosis or anti-atherosclerotic development amount of a compound of formula II as described in claim 1, or a pharmaceutically acceptable salt thereof, to the mammal.

### Claim 16 (depends on 1)

The compound of claim 1, wherein A is carboxy.

### Claim 17 (depends on 1)

The compound of claim 1, wherein W is —C(═O)—.

### Claim 18 (depends on 1)

The compound of claim 1, wherein W1 is O.

### Claim 19 (depends on 1)

The compound of claim 1, wherein the polyether is a methoxy-terminated poly(ethylene oxide) having between about 2 and about 150 repeating units.

### Claim 20 (depends on 1)

The compound of claim 1, wherein each R3 is independently (C1-C8)alkyl wherein each (C1-C8)alkyl is independently substituted with two or more —O(C═O)R1 groups.