# US 8,785,475 B2 · Lipoic acid derivatives

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- Number: US 8,785,475 B2
- Document ID: US8785475B2
- Status: Granted
- Kind: B2
- Application number: 12/105,096
- Filed: 2008-04-17
- Published: 2008-10-23
- Granted: 2014-07-22
- Earliest claimed: 2007-04-18
- Assignees: Cornerstone Pharmaceuticals, Inc.
- Applicants: Paul Bingham; Tom Kwok; Zuzana Zachar
- Inventors: Paul Bingham; Tom Kwok; Zuzana Zachar
- Web page: https://patentgrep.com/patent/US8785475B2

## CPC

- C07C 323/52: the carbon skeleton being acyclic and saturated
- A61P 11/06: Antiasthmatics
- A61P 17/04: Antipruritics
- A61P 17/06: Antipsoriatics
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/14: Decongestants or antiallergics
- A61P 35/00: Antineoplastic agents
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 323/56: the carbon skeleton containing six-membered aromatic rings
- C07C 323/60: with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
- C07C 327/32: having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C07D 207/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 213/64: attached in position 2 or 6
- C07D 213/70: Sulfur atoms
- C07D 213/81: Amides; Imides
- C07D 277/74: Sulfur atoms substituted by carbon atoms
- C07D 339/08: Six-membered rings
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 495/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07F 17/02: of metals of Groups 8, 9 or 10 of the Periodic Table
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Lipoic acid derivatives and pharmaceutical formulations containing lipoic acid derivatives are useful in the treatment and prevention of disease characterized by disease cells that are sensitive to lipoic acid derivatives.

## Claims

### Claim 1

A lipoic acid derivative selected from the group consisting of:

### Claim 2 (depends on 1)

A pharmaceutical formulation comprising (a) a therapeutically effective amount of at least one lipoic acid derivative of claim 1 and (b) at least one pharmaceutically acceptable additive.

### Claim 3 (depends on 2)

The pharmaceutical formulation of claim 2, wherein the at least one pharmaceutically acceptable additive is selected from the group consisting of solvents, diluents, surfactants, solubilizers, preservatives, buffers, and combinations thereof.

### Claim 4 (depends on 2)

The pharmaceutical formulation of claim 2, wherein the at least one lipoic acid derivative is present in an amount to provide from about 0.001 mg/m2 to about 10 g/m2.

### Claim 5 (depends on 1)

A method of treating lung cancer in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of at least one lipoic acid derivative according to claim 1.

### Claim 6 (depends on 5)

The method of claim 5, wherein the at least one lipoic acid derivative is in a pharmaceutical formulation further comprising at least one pharmaceutically acceptable additive.

### Claim 7

A lipoic acid derivative having the following formula:
wherein R1 and R2 are independently a heteroaryl selected from the group consisting of benzothiazolyl, quinolinyl, or 7-chloroquinolinyl;
x is 0-16; or a salt thereof.

### Claim 8

A lipoic acid derivative selected from the group consisting of:
or a salt thereof.

### Claim 9 (depends on 7)

A method of treating lung cancer in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of at least one lipoic acid derivative of claim 7.

### Claim 10 (depends on 1)

A method of treating melanoma or adenocarcinoma in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of at least one lipoic acid derivative of claim 1.

### Claim 11 (depends on 7)

A method of treating melanoma or adenocarcinoma in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of at least one lipoic acid derivative of claim 7.