# US 8,541,458 B2 · Oxabicycloheptanes and oxabicycloheptenes, their preparation and use

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- Number: US 8,541,458 B2
- Document ID: US8541458B2
- Status: Granted
- Kind: B2
- Application number: 13/493,816
- Filed: 2012-06-11
- Published: 2012-10-18
- Granted: 2013-09-24
- Earliest claimed: 2008-08-01
- Assignees: Lixte Biotechnology, Inc.
- Applicants: John S. Kovach; Francis Johnson
- Inventors: John S. Kovach; Francis Johnson
- Web page: https://patentgrep.com/patent/US8541458B2

## CPC

- C07D 307/00: Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61P 25/00: Drugs for disorders of the nervous system
- 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 31/10: Antimycotics
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

This invention provides compounds having the structure which may be used for the treatment of tumors.

## Claims

### Claim 1

A compound having the structure
wherein
bond αis present or absent;
R1 and R2 is each independently H, O−O or OR9,
where R9 , is H, alkyl, alkenyl, alkynyl or aryl,
or H1 and R2, together are ═O;
R3 is OH
R4 is
R5 and R6 is each independently H, OH, or R5 and R6 taken together are ═O; and
R7 and R8 is each independently H, F, Cl, Br, SO2Ph, CO2CH3, or SR13,
where R13 is H, aryl or a alkyl, alkenyl or alkynyl,
or a salt or enantiomer of the compound.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound has the structure

### Claim 3 (depends on 1)

The compound of claim 1, wherein bond α is present.

### Claim 4 (depends on 1)

The compound of claim 1, wherein bond α is absent.

### Claim 5 (depends on 1)

The compound of claim 1, having the structure
or a salt of the compound.

### Claim 6 (depends on 1)

The compound of claim 1, having the structure
or a salt of the compound.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 8 (depends on 5)

A process for preparing the compound of claim 5 comprising
(a) reacting a compound of the structure
with a compound having the structure
to form an anhydride having the structure
(b) reacting the anhydride having the above structure with a nucleophile having the structure
to form compound having the structure
wherein
R3 is OH and R4 is
R7 and R8 are each H,
(c) reacting the product of step (b) with hydrogen in the presence of a catalyst to form a compound having the structure
wherein
R3 is OH and R4 is
R7 and R8 are each H.

### Claim 9 (depends on 6)

A process for preparing the compound of claim 6 comprising
(a) reacting a compound of the structure
with a compound having the structure
to form an anhydride having the structure
(b) reacting the anhydride having the above structure with a nucleophile having the structure
to form compound having the structure
wherein
R3 is OH and R4 is
R7 and R8 are each H.