Pharmacologically active agents containing esterified phosphonates and methods for use thereof

• US 8,193,167 B2
• Filed: 12/10/2009
• Issued: 06/05/2012
• Est. Priority Date: 02/05/2004
• Status: Expired due to Fees

• Current Assignee: The United States of America As Represented By The Secretary of Agriculture, Regents of the University of California (University of California)
• Original Assignee: The United States of America As Represented By The Secretary of Agriculture, Regents of the University of California (University of California)
• Inventors: Hostetler, Karl Y., Wan, W. Brad
• Primary Examiner(s): GOON, SCARLETT Y
• Application Number:
  US12/635,644
• Publication Number:
  US 20100273742A1
• Time in Patent Office: 908 Days
• Field of Search: 514/75, 514/143, 568/8, 544/3
• US Class Current: 514/75
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/22 for herpes viruses
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07F 9/65586 at least one of the hetero rings does not contain nitrogen as ring hetero atom
• CPC Class Codes: C07F 9/65616 containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
• CPC Class Codes: C07F 9/657181 the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
• CPC Class Codes: C07F 9/65719 the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonous acid derivative

Abstract

Compounds and compositions are provided for treatment, prevention, or amelioration of a variety of medical disorders associated with viral infections, cell proliferation and bone metabolism. The compounds provided herein are alkyl esters of phosphonates.

Claims

1. A compound having the following formula:

P^x—

O—

R,

or a pharmaceutically acceptable derivative thereof,

wherein P^x is a cyclic cidofovir, O is an oxygen atom, and R is selected from the group consisting of eicosyl, docosyl and tetracosyl.

2. The compound of claim 1, wherein R is eicosyl or docosyl.

3. The compound of claim 1, wherein the compound is eicosyl cyclic cidofovir.

4. The compound of claim 1, wherein the compound is docosyl cyclic cidofovir.

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

6. An article of manufacture, comprising packaging material and the compound of claim 1, contained within the packaging material, wherein the compound is effective for treatment of a disease associated with a viral infection and the packaging material includes a label that indicates that the compound is used for treatment of a disease associated with the viral infection, wherein said viral infection is influenza, hepatitis B virus, hepatitis C virus, cytomegalovirus, Varicella zoster virus, Herpes simplex virus type 1, Herpes simplex virus type 2, Herpes virus type 6, Herpes virus type 8, Epstein Barr virus, retrovirus, orthopox virus, ebola virus, adenovirus or papilloma virus.

7. A method for treating a viral infection in a mammal, wherein the method comprises administering to a subject in need thereof an effective amount of the compound of claim 1, wherein the viral infection is caused by influenza, hepatitis B virus, hepatitis C virus, cytomegalovirus, Varicella zoster virus, Herpes simplex virus type 1, Herpes, simplex virus type 2, Herpes virus type 6, Herpes virus type 8, Epstein Barr virus, retrovirus, orthopox virus, ebola virus, adenovirus or papilloma virus.

8. The method according to claim 7, wherein the viral infection is an orthopox viral infection selected from the group consisting of smallpox, cowpox, camelpox, and monkeypox.

9. The method according to claim 7, wherein the viral infection is a herpes viral infection.

10. The method according to claim 7, wherein the viral infection is a hepatitis B or a hepatitis C infection.