# US 7,612,085 B2 · Sigma 2 receptor ligands and therapeutic uses therefor

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- Number: US 7,612,085 B2
- Document ID: US7612085B2
- Status: Granted
- Kind: B2
- Application number: 11/776,533
- Filed: 2007-07-11
- Published: 2008-07-03
- Granted: 2009-11-03
- Earliest claimed: 2006-07-11
- Assignees: Washington University
- Inventors: Robert H. Mach; Zhude Tu; Wenhua Chu; Suwanna Vangveravong; Richard Hotchkiss; William Hawkins; Rebecca Aft
- Web page: https://patentgrep.com/patent/US7612085B2

## CPC

- C07D 451/14: containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
- A61P 35/00: Antineoplastic agents
- C07D 451/02: containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A series of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs are disclosed, as well as methods of their preparation. Their affinities for sigma (σ1 and σ2) receptors are described. Two new compounds, N-(9-(4-aminobutyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate and N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate, are shown to have a high affinity and selectivity for σ2 versus σ1 receptors. Among the disclosed compounds are biotinylated and fluorescent analogs. These compounds can serve as probes to the σ2 receptor. In addition, some disclosed compounds can induce apoptotic cell death by both caspase-dependent and caspase-independent mechanisms, and are effective for treatment of tumors. The compounds can be used as chemotherapeutics or chemosensitizers in the treatment of a wide variety of solid tumors.

## Claims

### Claim 1

A compound or a salt thereof selected from the group consisting of

### Claim 2 (depends on 1)

A compound or a salt thereof in accordance with claim 1, wherein the compound is

### Claim 3 (depends on 1)

A pharmaceutical composition comprising at least one compound or salt thereof of claim 1.